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

HRID 1012102Notes

Reaction equation

HRID 1012102 reaction equation
ClC1C=CC=C(Cl)C=1C(NC1C(C2NC3C=CC(CN4CCOCC4)=CC=3N=2)=NNC=1)=O.[Cl:33][C:34]1[CH:50]=[CH:49][CH:48]=[C:47]([F:51])[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].[NH2:52][C:53]1[CH:54]=[C:55]([C:60]([N:62]2[CH2:67][CH2:66][O:65][CH2:64][CH2:63]2)=[O:61])[CH:56]=[CH:57][C:58]=1[NH2:59]>>[Cl:33][C:34]1[CH:50]=[CH:49][CH:48]=[C:47]([F:51])[C:35]=1[C:36]([NH:38][C:39]1[C:40]([C:44]2[NH:59][C:58]3[CH:57]=[CH:56][C:55]([C:60]([N:62]4[CH2:63][CH2:64][O:65][CH2:66][CH2:67]4)=[O:61])=[CH:54][C:53]=3[N:52]=2)=[N:41][NH:42][CH:43]=1)=[O:37]

Participants

4

Reactant 3

HCID 22411123(3,4-diaMinophenyl)(Morpholino)MethanoneHCID 178522426HCID 178522426, compoundHCID 1785249534-(2-Chloro-6-fluorobenzamido)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 1785224352-chloro-6-fluoro-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), but using 4-(2-chloro-6-fluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid (Example 95A) and (3,4-diamino-phenyl)-morpholin-4-yl-methanone (Example 94B) to give 2-chloro-6-fluoro-N-{3-[5-(morpholine-4-carbonyl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}-benzamide (18 mg) as a beige solid. (LC/MS: Rt 2.89, [M+H]+ 469.15).

Sources & evidence

ORD record
ord-e8e9adbfbbd34434b57cbc3d1db700c7
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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