Hydrazine hydrate (1:1) → 2-Amino-5-(6-morpholin-4-ylpyridin-3-yl)thiophene-3-carboxamide

HRID 1967150Notes

Reaction equation

[N:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[S:17][C:16]([N+:18]([O-])=O)=[C:15]([C:21]([NH2:23])=[O:22])[CH:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.NN>CO.[Fe](Cl)(Cl)Cl>[NH2:18][C:16]1[S:17][C:13]([C:10]2[CH:11]=[N:12][C:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:8][CH:9]=2)=[CH:14][C:15]=1[C:21]([NH2:23])=[O:22]

Participants

Conditions

Temperature: 65 °C

Procedure

5-(6-Morpholin-4-ylpyridin-3-yl)-2-nitrothiophene-3-carboxamide (2.77 g, 8.28 mmol), iron(III) chloride (0.03 g, 0.17 mmol), and hydrazine monohydrate (1.34 ml, 27.3 mmol) were combined in methanol (166 ml) and the reaction mixture was purged with nitrogen. The reaction was heated to 65° C. for 3 hours. After cooling to room temperature, the reaction mixture was filtered and solid was washed with methanol. Silica gel was added to the filtrate and the mixture was concentrated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/methanol to give the title compound as an orange solid.

Workup

customthe reaction mixture was purged with nitrogen
temperatureAfter cooling to room temperature
filtrationthe reaction mixture was filtered
washsolid was washed with methanol
additionSilica gel was added to the filtrate
concentrationthe mixture was concentrated
customThe residue was purified by column chromatography on silica gel
washeluting with ethyl acetate/methanol

Sources & evidence

ORD record: ord-347bcde289fe4cb1bee722184aad985a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420695B2

Reaction notes

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