Hydrazine hydrate (1:1) → HCID 178505619, compound

HRID 1875436Notes

Reaction equation

O.[NH2:2][NH2:3].Cl[C:5]1[C:6]([C:12](=O)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[N:7][CH:8]=[C:9]([Cl:11])[CH:10]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[Cl:11][C:9]1[CH:10]=[C:5]2[NH:3][N:2]=[C:12]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[F:20])[C:6]2=[N:7][CH:8]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A little DMAP and 238 mg (4.75 mmol) of hydrazine hydrate are added to a solution of 1.35 g (4.75 mmol) of 1-(3,5-dichloropyridin-2-yl)-2-(2-fluorophenyl)ethanone from example 2A in 12 ml of pyridine. The mixture is heated in a closed vessel in a microwave at 160° C. for 20 min and then concentrated in vacuo, and the residue is purified by chromatography on silica gel (eluent: dichloromethane/methanol 100:3). 507 mg (41% of theory) of the title compound and 388 mg of the uncyclized hydrazone are obtained. The latter is heated anew in 5 ml of DMF in the microwave at 200° C. for 1.5 h. The solution is concentrated and the residue is purified by preparative HPLC. A further 176 mg (12% of theory) of the title compound are obtained in this way.

Workup

concentrationconcentrated in vacuo
customthe residue is purified by chromatography on silica gel (eluent: dichloromethane/methanol 100:3)

Sources & evidence

ORD record: ord-78c12d8dd53c4043bfdeac471c2a2b66
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309551B2

Reaction notes

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