(3,4-diaMinophenyl)(Morpholino)Methanone → 2,6-difluoro-4-methoxy-N-{3-[5-(morpholine-4-carbonyl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}-benzamide

HRID 1012103Notes

Reaction equation

HRID 1012103 reaction equation
ClC1C=CC=C(Cl)C=1C(NC1C(C2NC3C=CC(CN4CCOCC4)=CC=3N=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].[NH2:54][C:55]1[CH:56]=[C:57]([C:62]([N:64]2[CH2:69][CH2:68][O:67][CH2:66][CH2:65]2)=[O:63])[CH:58]=[CH:59][C:60]=1[NH2:61]>>[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:61][C:60]3[CH:59]=[CH:58][C:57]([C:62]([N:64]4[CH2:65][CH2:66][O:67][CH2:68][CH2:69]4)=[O:63])=[CH:56][C:55]=3[N:54]=2)=[N:41][NH:42][CH:43]=1)=[O:37]

Participants

4

Reactant 3

HCID 22411123(3,4-diaMinophenyl)(Morpholino)MethanoneHCID 1784929554-(2,6-difluoro-4-methoxy-benzoylamino)-1H-pyrazole-3-carboxylic acidHCID 178522426HCID 178522426, compound

Product 1

HCID 1784929542,6-difluoro-4-methoxy-N-{3-[5-(morpholine-4-carbonyl)-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), however using 4-(2,6-difluoro-4-methoxy-benzoylamino)-1H-pyrazole-3-carboxylic acid (Example 96A) and (3,4-diamino-phenyl)-morpholin-4-yl-methanone (Example 94B) to give 2,6-difluoro-4-methoxy-N-{3-[5-(morpholine-4-carbonyl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}-benzamide (24 mg) as a beige solid. (LC/MS: Rt 2.94, [M+H]+ 483.20).

Sources & evidence

ORD record
ord-1719edef12114a91bb296a49a214bb6f
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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