Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 59522577, compound

HRID 388923Notes

Reaction equation

HRID 388923 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[NH:15][C:14]2[CH:16]=[CH:17][C:18]([C:20]([OH:22])=O)=[CH:19][C:13]=2[N:12]=1)([CH3:3])[CH3:2].[N:23]1([CH2:29][CH2:30][NH:31][C:32]2[C:40]3[C:35](=[CH:36][C:37]([NH2:41])=[CH:38][CH:39]=3)[NH:34][N:33]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[N:23]1([CH2:29][CH2:30][NH:31][C:32]2[C:40]3[C:35](=[CH:36][C:37]([NH:41][C:20]([C:18]4[CH:17]=[CH:16][C:14]5[N:15]=[C:11]([NH:10][C:5]6[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=6[CH:1]([CH3:3])[CH3:2])[NH:12][C:13]=5[CH:19]=4)=[O:22])=[CH:38][CH:39]=3)[NH:34][N:33]=2)[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

4

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68444836HCID 68444836, compoundHCID 178438959HCID 178438959, compound

Product 1

HCID 59522577HCID 59522577, compound

Procedure

The ester obtained as above was hydrolyzed using general procedure C to yield 2-(2-isopropylphenylamino)-1H-benzimidazole-5-carboxylic acid. The carboxylic acid (0.25 mmol) was coupled with 3-(2-morpholin-4-yl-ethylamino)-1H-indazol-6-ylamine (0.25 mmol) using HBTU employing general procedure D. The product, 2-(2-Isopropylphenylamino)-3H-benzimidazole-5-carboxylic acid [3-(2-morpholin-4-yl-ethylamino)-1H-indazol-6-yl]-amide, was obtained after purification by silica gel chromatography using DCM/methanol as eluent. MS: m/z 539 (M+H)+.

Sources & evidence

ORD record
ord-2ee06817bbec4e928118f4d73b958261
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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