Ammonia → HCID 178508386, compound

HRID 1710366Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[NH:24][C:23](=S)[CH2:22][CH2:21][CH2:20][CH2:19]4)[NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:26]>CO>[C:1]1([C:7]2[CH:8]=[C:9]3[N:15]=[C:14]([CH2:16][CH2:17][CH:18]4[N:24]=[C:23]([NH2:26])[CH2:22][CH2:21][CH2:20][CH2:19]4)[NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

65 mg of 7-[2-(6-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-thione (compound A1) are suspended in 4.3 ml of methanol containing ammonia (strength: 7.0 M) and heated at 50° C. for 90 hours. Subsequently, the reaction mixture is evaporated to dryness and purified by flash chromatography on LiChroprep-NH2® (eluent gradient: dichloromethane/0-100 vol. % methanol), and lyophilized from 2.0 ml of water, 5.0 ml of dioxane to afford 29.5 mg of the title compound as an amorphous, colorless solid of m.p. 117° C. (decomp.). ESI-MS: 334.3 (MH+). TLC: Rf=0.35 (LiChroprep-NH2® HPTLC, methanol/water 10:1 parts by volume).

Workup

customSubsequently, the reaction mixture is evaporated to dryness
custompurified by flash chromatography on LiChroprep-NH2® (eluent gradient: dichloromethane/0-100 vol. % methanol)

Sources & evidence

ORD record: ord-51547afed8134322bacb0dde7e9ab27d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790710B2

Reaction notes

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