Benzoyl isothiocyanate → HCID 178522524, compound

HRID 1452746Notes

Reaction equation

Br[C:2]1[C:6]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:5][NH:4][C:3]=1[NH2:12].[C:13]([N:21]=[C:22]=[S:23])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCOCC1>[S:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:6]1[C:2]2[S:23][C:22]([NH:21][C:13](=[O:20])[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[N:12][C:3]=2[NH:4][N:5]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirring solution of 4-bromo-5-thiophen-2-yl-2H-pyrazol-3-ylamine (50 mg, 0.205 mmol) in dioxane (1 mL) was added benzoylisothiocyanate (30 μL, 0.225 mmol) dropwise. The reaction mixture was stirred at 90° C. for 17 h. It was then cooled to room temperature and partitioned between ethyl acetate and a saturated aqueous solution of sodium bicarbonate. The organic layer was washed twice with a saturated aqueous solution of sodium bicarbonate, then with brine, and adsorbed on silica gel. Purification on silica gel with 0-80% ethyl acetate in hexane as eluent provided 54 mg (80%) of N-(3-thiophen-2-yl-1H-pyrazolo[3,4-d]thiazol-5-yl)-benzamide as a beige solid. 1H-NMR (d6-DMSO) δ: 13.5 and 13.6 (2 broad s, 1H, NH+tautomer), 12.9 (broad s, 1H, NH), 8.1 (d, 2H), 7.68 and 7.85 (2 dd, 1H, tautomers), 7.66 (t, 1H), 7.58 (t, 2H), 7.34 and 7.53 ( 2 d, 1H, tautomers), 7.17 and 7.22 (2 t, 1H, tautomers); HPLC/MS m/z: 327 [MH]+.

Workup

temperatureIt was then cooled to room temperature
custompartitioned between ethyl acetate
washThe organic layer was washed twice with a saturated aqueous solution of sodium bicarbonate
customPurification on silica gel with 0-80% ethyl acetate in hexane as eluent

Sources & evidence

ORD record: ord-26cf16beb521436381b88edbaf7b4233
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473783B2

Reaction notes

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