Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178521763, compound

HRID 388933Notes

Reaction equation

HRID 388933 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[NH:11][C:12]2[CH:18]=[C:17]([C:19]([OH:21])=O)[CH:16]=[CH:15][C:13]=2[N:14]=1.[N:22]1([CH2:28][C:29]2[C:37]3[C:32](=[CH:33][C:34]([NH2:38])=[CH:35][CH:36]=3)[NH:31][N:30]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[N:22]1([CH2:28][C:29]2[C:37]3[C:32](=[CH:33][C:34]([NH:38][C:19]([C:17]4[CH:16]=[CH:15][C:13]5[N:14]=[C:10]([NH:9][C:3]6[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=6[Cl:1])[NH:11][C:12]=5[CH:18]=4)=[O:21])=[CH:35][CH:36]=3)[NH:31][N:30]=2)[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1

Participants

4

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68442850HCID 68442850, compoundHCID 178507303HCID 178507303, compound

Product 1

HCID 178521763HCID 178521763, compound

Procedure

The ester obtained as above was hydrolyzed using general procedure C to yield 2-(2,4-dichlorophenylamino)-3H-benzimidazole-5-carboxylic acid. The carboxylic acid (0.25 mmol) was coupled with 3-(morpholin-4-yl)methyl-1H-indazol-6-ylamine (0.25 mmol) using HBTU employing general procedure D. The product, 2-(2,4-dichlorophenylamino)-3H-benzimidazole-5-carboxylic acid (3-morpholin-4-ylmethyl-1H-indazol-6-yl)-amide, was obtained as a light brown solid after purification by silica gel chromatography using DCM/methanol as eluent. MS: m/z 536 (M+H)+.

Sources & evidence

ORD record
ord-afdb081400f54fe8a0d76d55da64e92d
Source dataset
uspto-grants-2013_02
Patent number
US08377983B2

Reaction notes

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