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

HRID 1367904Notes

Reaction equation

HRID 1367904 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([OH:14])=O)[N:3]=1.[NH:15]1[CH:19]=[CH:18][N:17]=[C:16]1[NH:20][C:21]([C:23]1[C:31]2[NH:30][C:29]([NH2:32])=[N:28][C:27]=2[CH:26]=[CH:25][CH:24]=1)=[O:22].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:17]1[CH:18]=[CH:19][N:15]=[C:16]1[NH:20][C:21]([C:23]1[C:31]2[N:30]=[C:29]([NH:32][C:12]([C:4]3[N:3]=[C:2]([CH3:1])[C:11]4[C:6]([CH:5]=3)=[CH:7][CH:8]=[CH:9][CH:10]=4)=[O:14])[NH:28][C:27]=2[CH:26]=[CH:25][CH:24]=1)=[O:22]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 189650101-Methylisoquinoline-3-carboxylic acidHCID 178508178HCID 178508178, compound

Product 1

HCID 580263491-methyl-isoquinoline-3-carboxylic acid [4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amideYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17.6 mg (15%) of 1-methyl-isoquinoline-3-carboxylic acid [4-(1H-imidazol-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide was synthesized according to General Procedure A using 55 mg (0.29 mmol) of 1-methyl-isoquinoline-3-carboxylic acid, 70 mg (0.29 mmol) of intermediate B (2-amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide), 144 mg (0.38 mmol) of HBTU, 0.264 mL (1.5 mmol) of DIEA in 0.8 mL of DMF stirring at 85° C. for 2 h. 1H-NMR (400 MHz, DMSO): 8.66 (s, 1H), 8.38 (d, 1H), 8.28 (d, 1H), 7.89 (m 4H), 7.34 (m, 1H), 6.85 (b, 2H), 3.07 (s, 3H) ppm. LCMS: 412 (M+1)+.

Sources & evidence

ORD record
ord-782edb17fa9a47c69cb895958b74a7f1
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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