Diisopropylethylamine → 1-(2-methylsulfanyl-ethyl)-isoquinoline-3-carboxylic acid [4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide

HRID 1910173Notes

Reaction equation

HRID 1910173 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:15]([OH:17])=O)[N:6]=1.[NH:18]1[CH:22]=[CH:21][N:20]=[C:19]1[NH:23][C:24]([C:26]1[C:34]2[NH:33][C:32]([NH2:35])=[N:31][C:30]=2[CH:29]=[CH:28][CH:27]=1)=[O:25].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:20]1[CH:21]=[CH:22][N:18]=[C:19]1[NH:23][C:24]([C:26]1[C:34]2[N:33]=[C:32]([NH:35][C:15]([C:7]3[N:6]=[C:5]([CH2:4][CH2:3][S:2][CH3:1])[C:14]4[C:9]([CH:8]=3)=[CH:10][CH:11]=[CH:12][CH:13]=4)=[O:17])[NH:31][C:30]=2[CH:29]=[CH:28][CH:27]=1)=[O:25]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669404611-(2-Methylsulfanyl-ethyl)-isoquinoline-3-carboxylic acidHCID 178508178HCID 178508178, compound

Product 1

HCID 580265661-(2-methylsulfanyl-ethyl)-isoquinoline-3-carboxylic acid [4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amideYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

42.4 mg (0.171 mmol) of 1-(2-methylsulfanyl-ethyl)-isoquinoline-3-carboxylic acid was reacted with 34 mg (0.14 mmol) of intermediate B (2-amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide), 114 mg (0.3 mmol) of HBTU and 0.106 mL (0.6 mmol) of DIEA in 0.8 mL of DMF stirring at 85° C. for 3 h according to the general procedure A. 44.3 mg (55%) of 1-(2-methylsulfanyl-ethyl)-isoquinoline-3-carboxylic acid [4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide was obtained. LCMS: 472 (M+1)+.

Sources & evidence

ORD record
ord-40e547013f3b44bfa5aab6ed5a9248a7
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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