Category: 180995-12-4

Synthetic Route of 180995-12-4, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.180995-12-4, name is 2,4-Dichloronicotinonitrile, molecular formula is C6H2Cl2N2, molecular weight is 173, as common compound, the synthetic route is as follows.

To a mixture of 5-amino-1-methyl-1 H-benzo[d]imidazol-2(3/-/)-one (750 mg, 4.6 mmol) and 2,4-dichloropyridine-3-carbonitrile (760 mg, 4.4 mmol) under argon was added DMA (10 mL) followed by DIPEA (0.90 mL, 5.19 mmol) . The reaction mixture was heated at 120C under microwave irradiation for 45 min then allowed to cool to rt and added dropwise to a stirring mixture of methanol:water (1 : 1 ; 120 mL). The resulting precipitate was filtered, washed with water (2 x 25 mL) and diethyl ether (2 x 30 mL) affording 2-chloro-4-[(1-methyl- 2-oxo-3/-/-benzimidazol-5-yl)amino]pyridine-3-carbonitrile (1297 mg, 99%, 4.3 mmol) as a beige solid. 1 H NMR (500 MHz, DMSO-cfe) delta 10.95 (br s, 1 H), 9.39 (br s, 1 H), 7.99 (d, J = 6.2 Hz, 1 H), 7.13 (d, J = 8.3 Hz, 1 H), 6.95 (dd, J = 8.3, 1.9 Hz, 1 H), 6.90 (d, J = 1.9 Hz, 1 H), 6.65 (d, J = 6.2 Hz, 1 H).

The chemical industry reduces the impact on the environment during synthesis 180995-12-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BELLENIE, Benjamin Richard; CARTER, Michael Keith; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; LLOYD, Matthew Garth; VARELA RODRIGUEZ, Ana; (381 pag.)WO2018/215801; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 180995-12-4 , The common heterocyclic compound, 180995-12-4, name is 2,4-Dichloronicotinonitrile, molecular formula is C6H2Cl2N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Ethyl 6-amino-4-((1-((te/f-butoxycarbonyl)amino)propan-2-yl)amino)-1 -methyl-2- oxo-1 , 2-dihydroquinoline-3-carboxylate (from step 2; 50 mg, 0.12 mmol), 2,4- dichloronicotinonitrile (21 mg, 0.12 mmol) and DIPEA (62 uL, 0.36 mmol) were combined in a microwave vial and dissolved in NMP (1 mL). The reaction mixture was heated at 110 C under microwave irradiation for 90 min, followed by heating at 110 C in a heating block for a further 8 h. The reaction mixture was cooled to rt, and trifluoroacetic acid (183 uL, 2.39 mmol) was added and the reaction mixture was stirred at 70 C for 30 min. The reaction mixture was cooled to rt, and DIPEA (0.5 mL) was added. The reaction mixture was stirred at 70 C for 4 h. The reaction mixture was cooled to rt and partitioned between EtOAc (20 mL) and water (20 mL). The aqueous layer was extracted once with EtOAc (20 mL) and the organic extracts were combined, washed twice with brine, dried (MgS04), and concentrated in vacuo affording the title compound (62 mg, 94%) as a brown oil which was used without further purification. LCMS (Method T4); RT 2.91 min; m/z 555.211 [M+H]+.

The synthetic route of 180995-12-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; BELLENIE, Benjamin Richard; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; HUCKVALE, Rosemary; COLLIE, Gavin; MENICONI, Mirco; BRENNAN, Alfie; LLOYD, Matthew Garth; (222 pag.)WO2019/197842; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 180995-12-4, Adding some certain compound to certain chemical reactions, such as: 180995-12-4, name is 2,4-Dichloronicotinonitrile,molecular formula is C6H2Cl2N2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 180995-12-4.

(114a) 2-chloro-4-(ethylthio)nicotinonitrile; N,N -dimethylacetamide (1 mL) solution of sodium thioethoxide (93 mg, 1.1 mmol) was added to N,N -dimethylacetamide (1 mL) solution of 2,4-dichloronicotinonitrile (173 mg, 1.00 mmol) which was produced in Example 111 (111a) at 0C and the mixture was stirred at room temperature for one hour. Water (3 mL) was added to the reaction liquid, and generated powder was separated by filtration and further purified by silica gel column chromatography (hexane/ethyl acetate =3:1) and the title compound was obtained (44 mg, yield 22%). Pale yellow powder Mp 97-98C; IR (KBr) numax 2226, 1556, 1518, 1431, 1379, 1199, 819 cm-1; 1H NMR(CDCl3, 500 MHz) delta 1.46 (3H, t, J = 7.3 Hz), 3.12 (2H, q, J = 7.3 Hz), 7.11 (1H, d, J = 5.9 Hz), 8.33 (1H, d, J = 5.9 Hz); HRMS m/z calcd for C8H7N235ClS 198.0018, found 198.0011; MS (EI) m/z: 198 [M+], 183, 170, 165, 147, 134, 126, 108, 98, 76, 69, 64, 46.

According to the analysis of related databases, 180995-12-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sankyo Company, Limited; EP1764367; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem