2-Aminothiazole → 2-(6-chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide

HRID 85098Notes

Reaction equation

HRID 85098 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]([OH:19])=O)[C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[S:20]1[CH:24]=[CH:23][N:22]=[C:21]1[NH2:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]([NH:25][C:21]4[S:20][CH:24]=[CH:23][N:22]=4)=[O:19])[C:10]=3[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 21552-AminothiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866537842-(6-chloropyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid

Product 1

HCID 866537852-(6-chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamideYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(6-Chloropyridin-3-yl)-1H-benzo[d]imidazole-4-carboxylic acid (6; 340 mg, 1.24 mmol) was taken up in DMF (5 mL) along with thiazol-2-amine (4; 125 mg, 1.24 mmol) and HATU (943 mg, 2.48 mmol). DIEA (0.41 mL, 2.48 mmol) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and the resulting solids were collected by filtration. Purification by silica gel chromatography (pentane/EtOAc) afforded 2-(6-chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide 7 as a pale yellow solid (215 mg, yield: 52%). MS (ESI) calcd for C16H10ClN5OS: 355.03; found: 356 [M+H].

Workup

  1. filtrationthe resulting solids were collected by filtration
  2. customPurification by silica gel chromatography (pentane/EtOAc)

Sources & evidence

ORD record
ord-d487be58354c464eb8014a8fed85fbe5
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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