Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 1H-indazole-6-carboxylic acid [2-(2-isopropylphenylamino)-3H-benzimidazol-5-yl]-amide
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=2)[CH:3]=[N:2]1.[CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]1[NH:27][C:26]2[CH:28]=[CH:29][C:30]([NH2:32])=[CH:31][C:25]=2[N:24]=1)([CH3:15])[CH3:14].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]1[NH:24][C:25]2[CH:31]=[C:30]([NH:32][C:10]([C:7]3[CH:8]=[C:9]4[C:4]([CH:3]=[N:2][NH:1]4)=[CH:5][CH:6]=3)=[O:12])[CH:29]=[CH:28][C:26]=2[N:27]=1)([CH3:15])[CH3:14]Participants
4
Reactant 3
Product 1
Procedure
Methyl Indazole-6-carboxylate (4 mmol; Batt et al, J. Med. Chem. 2000, 43, 41-58) was hydrolyzed as in general procedure C to obtain 1H-Indazole-6-carboxylic acid. The carboxylic acid (0.5 mmol) was coupled with aforementioned N2-(2-isopropylphenyl)-1H-benzimidazole-2,5-diamine (0.5 mmol) using HBTU as described in general procedure D to yield 1H-indazole-6-carboxylic acid [2-(2-isopropylphenylamino)-3H-benzimidazol-5-yl]-amide as an off-white solid. MS: m/z 411 (M+H)+.
Sources & evidence
- ORD record
- ord-314469771384442d90167e3a2fb79f53
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377983B2
Reaction notes
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