Isoniazid → HCID 178505583, compound

HRID 1272772Notes

Reaction equation

HRID 1272772 reaction equation
Cl.C(O[C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[NH:6])C.[C:23]([NH:31][NH2:32])(=O)[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>>[F:22][C:19]1[CH:18]=[CH:17][C:16]([C:10]2[C:9]3[C:13](=[CH:14][CH:15]=[C:7]([C:5]4[NH:6][C:23]([C:24]5[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=5)=[N:31][N:32]=4)[CH:8]=3)[NH:12][N:11]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 3767IsoniazidHCID 22479739ethoxy[3-(4fluorophenyl)(1H-indazol-5-yl)]methanimine hydrochloride

Product 1

HCID 178505583HCID 178505583, compoundYield 15.4%

Procedure

The procedure described in example 119 using ethoxy[3-(4-fluorophenyl)(1H-indazole-5-yl)]methanimine hydrochloride (200 mg, 0.62 mmol), triethylainine (0.25 mL, 1.86 mmol) and isonicotinic acid hydrazide (171.42 mg, 1.25 mmol) was followed to yield the title compound (34 mg, 15% yield). 1H NMR (DMSO-d6) δ 13.6 (s, 1H), 8.78–8.82 (m, 3H), 8.05–8.25 (m, 5H), 7.8 (d, 1H), 7.45 (t, 2H), ES-MS (m/z) 357 [M+1]+.

Sources & evidence

ORD record
ord-c5650b4584c744e29eccc5457f4c28bf
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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