4-(2,6-difluoro-4-methoxy-benzoylamino)-1H-pyrazole-3-carboxylic acid → 2,6-difluoro-4-methoxy-N-[3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide

HRID 1012098Notes

Reaction equation

HRID 1012098 reaction equation
ClC1C=CC=C(Cl)C=1C(NC1C(C2[NH:16][C:15]3[CH:17]=[CH:18][C:19]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:20][C:14]=3[N:13]=2)=NNC=1)=O.[F:33][C:34]1[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[C:47]([F:53])[C:35]=1[C:36]([NH:38][C:39]1[C:40]([C:44](O)=O)=[N:41][NH:42][CH:43]=1)=[O:37]>>[F:33][C:34]1[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[C:47]([F:53])[C:35]=1[C:36]([NH:38][C:39]1[C:40]([C:44]2[NH:16][C:15]3[CH:17]=[CH:18][C:19]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:20][C:14]=3[N:13]=2)=[N:41][NH:42][CH:43]=1)=[O:37]

Participants

3

Reactant 2

HCID 1784929554-(2,6-difluoro-4-methoxy-benzoylamino)-1H-pyrazole-3-carboxylic acidHCID 178522426HCID 178522426, compound

Product 1

HCID 1784929532,6-difluoro-4-methoxy-N-[3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide

Procedure

The compound was prepared in a manner analogous to 2,6-dichloro-N-[3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (Example 94E), but using 4-(2,6-difluoro-4-methoxy-benzoylamino)-1H-pyrazole-3-carboxylic acid to give 2,6-difluoro-4-methoxy-N-[3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (32 mg) as a pink solid. (LC/MS: Rt 1.99, [M+H]+ 469.21).

Sources & evidence

ORD record
ord-d48bac60de5b40e88a7796f5471be0f9
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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