Diisopropylethylamine → N-[7-[(1H-Imidazol-2-ylamino)carbonyl]-1H-benzimidazol-2-yl]thieno[2,3-c]pyridine-5-carboxamide

HRID 1367907Notes

Reaction equation

HRID 1367907 reaction equation
[S:1]1[C:5]2=[CH:6][N:7]=[C:8]([C:10]([OH:12])=O)[CH:9]=[C:4]2[CH:3]=[CH:2]1.[NH:13]1[CH:17]=[CH:16][N:15]=[C:14]1[NH:18][C:19]([C:21]1[C:29]2[NH:28][C:27]([NH2:30])=[N:26][C:25]=2[CH:24]=[CH:23][CH:22]=1)=[O:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH:15]1[CH:16]=[CH:17][N:13]=[C:14]1[NH:18][C:19]([C:21]1[C:29]2[N:28]=[C:27]([NH:30][C:10]([C:8]3[CH:9]=[C:4]4[CH:3]=[CH:2][S:1][C:5]4=[CH:6][N:7]=3)=[O:12])[NH:26][C:25]=2[CH:24]=[CH:23][CH:22]=1)=[O:20]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12277675thieno[2,3-c]pyridine-5-carboxylic acid(WXC09021)HCID 178508178HCID 178508178, compound

Product 1

HCID 58724481N-[7-[(1H-Imidazol-2-ylamino)carbonyl]-1H-benzimidazol-2-yl]thieno[2,3-c]pyridine-5-carboxamideYield 3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.6 mg (3%) of thieno[2,3-c]pyridine-5-carboxylic acid [4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide was prepared according to general procedure A using 54 mg (0.3 mmol) thieno[2,3-c]pyridine-5-carboxylic acid, 61 mg (0.25 mmol) intermediate B (2-amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide), 114 mg (0.3 mmol) of HBTU, 0.106 mL (0.6 mmol) of DIEA in 1 mL of DMF stirring at 85° C. for 1 h. LCMS: 404 (M+1)+.

Sources & evidence

ORD record
ord-e7b3ed38faad4b69aade29dd8f02db6d
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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