Hydrochloric Acid → HCID 178422584, compound

HRID 1604661Notes

Reaction equation

[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([CH3:29])[CH:27]=5)[C:22]([C:30]#[N:31])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][CH:25]=[C:26]([CH3:29])[CH:27]=5)[C:22]([C:30]5[NH:34][N:33]=[N:32][N:31]=5)=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 120 °C

Procedure

The mixture of 4-tert-butyl-2-{5-[(3-cyano-6-methylindol-1-yl)methyl]benzofuran-2-yl}thiazole (0.19 g), sodium azide (0.32 g) and ammonium chloride (0.30 g) in N,N-dimethylformamide (2 ml) was stirred at 120° C. for 72 hours. After being cooled to room temperature, the reaction mixture was poured into ice-water and the mixture was acidified with diluted hydrochloric acid. The resulting precipitates were collected by filtration and air-dried. The precipitates were subjected to column chromatography on silica gel and eluted with a mixture of dichloromethane and methanol. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 5-{1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-6-methylindol-3-yl}-1H-tetrazole (0.04 g).

Workup

temperatureAfter being cooled to room temperature
customThe resulting precipitates
filtrationwere collected by filtration
customair-dried
washeluted with a mixture of dichloromethane and methanol
additionThe fractions containing the objective compound
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-81ef435f66df48f0a89333fc3fd3d250
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994378

Reaction notes

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