Dimethyl Sulfoxide → HCID 135797569, compound

HRID 2412396Notes

Reaction equation

Cl.[NH2:2][C:3]1[C:4]2[C:5](=[N:15][N:16]([CH3:18])[N:17]=2)[NH:6][C:7]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:8]=2[N:9]=1.CS(C)=O.[CH3:23][N:24]1[CH2:29][CH2:28]N[CH2:26][CH2:25]1>C1(C)C=CC=CC=1>[F:14][C:11]1[CH:12]=[CH:13][C:7]2[NH:6][C:5]3=[N:15][N:16]([CH3:18])[N:17]=[C:4]3[C:3]([N:2]3[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]3)=[N:9][C:8]=2[CH:10]=1

Participants

Conditions

Temperature: 125 °C

Procedure

10-Amino-7-fluoro-2-methyl-2,4-dihydro-1,2,3-triazolo[4,5-b][1,5]benzodiazepine hydrochloride (2.68 g) was added to a mixture of dry dimethyl sulphoxide (10 ml), toluene (10 ml) and dry N-methyl piperazine (3.3 ml), which had been degassed with nitrogen for 20 minutes. The stirred solution was then heated at 125° C. (oil-bath) under nitrogen for five hours, cooled to room temperature, and distilled water (33.3 ml) added, keeping the temperature below 25° C. After stirring at 5° C. for half an hour, the suspension obtained was filtered off and dried at 70° C. under reduced pressure to leave a yellow crystalline solid, which was recrystallised from ethyl acetate/n hexane, melting point 195°-197° C.

Workup

customhad been degassed with nitrogen for 20 minutes
temperaturecooled to room temperature
distillationdistilled water (33.3 ml)
additionadded
customthe temperature below 25° C
customthe suspension obtained
filtrationwas filtered off
customdried at 70° C. under reduced pressure
customto leave a yellow crystalline solid, which
customwas recrystallised from ethyl acetate/n hexane, melting point 195°-197° C.

Sources & evidence

ORD record: ord-de82b0a52b584d38b4aac0c2196d0efe
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04492699

Reaction notes

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