1,2-Diamino-4,5-difluorobenzene → HCID 135839327, compound

HRID 724443Notes

Reaction equation

HRID 724443 reaction equation
N1C2C=CC=CC=2N=C1C1C2C(=CC(C(O)=O)=CC=2)NN=1.[OH:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]2[CH:40]=[C:39]3[C:35]([C:36]([CH:41]=O)=[N:37][NH:38]3)=[CH:34][CH:33]=2)=[O:31])=[CH:25][CH:24]=1.[F:43][C:44]1[C:49]([F:50])=[CH:48][C:47]([NH2:51])=[C:46]([NH2:52])[CH:45]=1>>[F:43][C:44]1[C:49]([F:50])=[CH:48][C:47]2[NH:51][C:41]([C:36]3[C:35]4[C:39](=[CH:40][C:32]([C:30]([NH:29][C:26]5[CH:25]=[CH:24][C:23]([OH:22])=[CH:28][CH:27]=5)=[O:31])=[CH:33][CH:34]=4)[NH:38][N:37]=3)=[N:52][C:46]=2[CH:45]=1

Participants

4

Reactant 3

HCID 27367551,2-Diamino-4,5-difluorobenzeneHCID 135839310319474-36-7HCID 178520042HCID 178520042, compound

Product 1

HCID 135839327HCID 135839327, compound

Procedure

Using the same procedure as for the synthesis of 3-(1H-benzoimidazol-2-yl)-1H-indazole-6-carboxylic acid in Example 53(a), step (ii), N-(4-hydroxyphenyl)-3-formyl-1H-indazole-6-carboxamide and 4,5-difluoro1,2-phenylenediamine gave 3-(5,6-difluoro-1H-benzoimidazol-2-yl)-N-(4-hydroxyphenyl)-1H-indazole-6-carboxamide as a tan solid. 1H NMR (DMSO-d6) δ 13.99 (1H, s), 13.27 (1H, s), 10.21 (1H, s), 9.25 (1H, s), 8.52 (1H, d, J=8.7 Hz), 8.21 (1H, s), 7.85 (1H, d, J=9.0 Hz), 7.80 (1H, t, J=9.8 Hz), 7.55 (2H, d, J=8.7 Hz), 7.47 (1H, t, J=9.8 Hz), 6.75 (2H, d, J=8.7 Hz). MS (APCI positive) 406.

Sources & evidence

ORD record
ord-d326b23cf1744d428a8980c405524ce3
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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