Sodium hydride → HCID 11168231, compound

HRID 2201974Notes

Reaction equation

HRID 2201974 reaction equation
Cl[C:2]1[S:3][C:4]([C:7]([N:9]([C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[O:8])=[CH:5][N:6]=1.[NH2:27][C:28]1[CH:33]=[C:32]([Cl:34])[N:31]=[C:30]([CH3:35])[N:29]=1.[H-].[Na+]>O1CCCC1>[Cl:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([CH3:25])[C:19]=1[N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[C:7]([C:4]1[S:3][C:2]([NH:27][C:28]2[CH:33]=[C:32]([Cl:34])[N:31]=[C:30]([CH3:35])[N:29]=2)=[N:6][CH:5]=1)=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2867546-Chloro-2-methylpyrimidin-4-amineHCID 11350299HCID 11350299, compound

Product 1

HCID 11168231HCID 11168231, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The first step of the process involves reacting 2-chlorothiazole with 2-chloro-6-methylphenylisocyanate in the presence of n-butyl lithium in tetrahydrofuran to obtain 2-chloro-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide. The second step involves reacting 2-chloro-N-(2-chloro-6-methylphenyl)-1,3-thiazole-5-carboxamide with 4-methoxybenzylchloride in the presence of sodium hydride in tetrahydrofuran to obtain 2-chloro-N-(2-chloro-6-methylphenyl)-N-(4-methoxybenzyl)-1,3-thiazole-5-carboxamide. The third step involves reacting 2-chloro-N-(2-chloro-6-methylphenyl)-N-(4-methoxybenzyl)-1,3-thiazole-5-carboxamide with 4-amino-6-chloro-2-methylpyrimidine in the presence of sodium hydride in tetrahydrofuran at reflux temperature to obtain N-(2-chloro-6-methylphenyl)-2-[(6-chloro-2-methylpyrimidin-4-yl)amino]-N-(4-methoxybenzyl)-1,3-thiazole-5-carboxamide. The fourth step involves reacting N-(2-chloro-6-methylphenyl)-2-[(6-chloro-2-methylpyrimidin-4-yl)amino]-N-(4-methoxybenzyl)-1,3-thiazole-5-carboxamide with trifluoromethanesulfonic acid and trifluoroacetic acid in dichloromethane to obtain N-(2-chloro-6-methylphenyl)-2-[(6-chloro-2-methylpyrimidin-4-yl)amino]-1,3-thiazole-5-carboxamide (Formula 1d).

Workup

  1. temperatureat reflux temperature

Sources & evidence

ORD record
ord-57174eaf2f224bfcbd56064e577e58f5
Source dataset
uspto-grants-2016_06
Patent number
US09365526B2

Reaction notes

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