Methanol → 3-(2-Fluorobenzyl)imidazo[1,5-a]pyridine-1-carbohydrazide

HRID 1875448Notes

Reaction equation

[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14](OCC)=[O:15])[N:6]=1.CO.O.[NH2:26][NH2:27]>C1COCC1>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[C:7]([C:14]([NH:26][NH2:27])=[O:15])[N:6]=1

Participants

Conditions

Temperature: 65 °C

Procedure

150 mg (0.50 mmol) of ethyl 3-(2-fluorobenzyl)imidazo[1,5-a]pyridine-1-carboxylate from example 7A are introduced into a mixture of 1 ml of methanol and 0.5 ml of THF, and 503 mg (10.1 mmol) of hydrazine hydrate are added. The mixture is heated firstly at 65° C. for 4 h and then at 90° C. for 10 h. It is then concentrated to dryness. The resulting crude product (157 mg, quantitative) is reacted without further purification.

Workup

additionare added
concentrationIt is then concentrated to dryness
customThe resulting crude product (157 mg, quantitative) is reacted without further purification

Sources & evidence

ORD record: ord-12d3531696564383bf142d24a11e0e74
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309551B2

Reaction notes

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