Ethyl orthoformate → 4-Chloro-7-cyclopentyl-7H-imidazo[4,5-c]pyridazine

반응식

[Cl:1][C:2]1[C:3]([NH2:14])=[C:4]([NH:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:5]=[N:6][CH:7]=1.[CH2:15](OC(OCC)OCC)C>>[Cl:1][C:2]1[C:3]2[N:14]=[CH:15][N:8]([CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[C:4]=2[N:5]=[N:6][CH:7]=1

참가 물질

반응물 2

HCID 31214Ethyl orthoformate

HCID 867232335-Chloro-N3-cyclopentylpyridazine-3,4-diamine

생성물 1

HCID 867232344-Chloro-7-cyclopentyl-7H-imidazo[4,5-c]pyridazine수율 51%

실험 절차

A mixture of 5-chloro-N-3-cyclopentylpyridazine-3,4-diamine (Preparation 12, 1.2 g, 5.64 mmol) and triethylorthoformate (10 mL) were heated to reflux for 1.5 hours. The reaction mixture was allowed to cool to room temperature, concentrated in vacuo and triturated with EtOAc (20 mL). The solid was filtered and the filtrate was reduced to dryness. The crude material was purified by silica gel column chromatography eluting with EtOAc to afford the title compound as a yellow solid in 51% yield, 902 mg.

후처리

temperaturewere heated
temperatureto reflux for 1.5 hours
concentrationconcentrated in vacuo
customtriturated with EtOAc (20 mL)
filtrationThe solid was filtered
customThe crude material was purified by silica gel column chromatography
washeluting with EtOAc

출처 및 근거

ORD 기록: ord-76aa0d6429ff4453a36bf33c1fe2c3c8
출처 데이터셋: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08952008B2

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