Benzoyl isothiocyanate → HCID 178522520, compound

HRID 1452749Notes

Reaction equation

HRID 1452749 reaction equation
Br[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[CH:8]=2)=[N:5][NH:4][C:3]=1[NH2:14].[C:15]([N:23]=[C:24]=[S:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCOCC1>[Cl:13][C:9]1[CH:8]=[C:7]([C:6]2[C:2]3[S:25][C:24]([NH:23][C:15](=[O:22])[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[N:14][C:3]=3[NH:4][N:5]=2)[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 178509106HCID 178509106, compound

Product 1

HCID 178522520HCID 178522520, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirring solution of 4-bromo-5-(3-chloro-phenyl)-2H-pyrazol-3-ylamine (50 mg, 0.183 mmol) in dioxane (1 mL) was added benzoyl isothiocyanate (27 μL, 0.202 mmol). The reaction mixture was stirred overnight at 90° C., cooled at room temperature, and partitioned between ethyl acetate and sodium bicarbonate. The organic layer was isolated and absorbed on silica gel. Purification on silica gel with 0-10% MeOH in CH2Cl2 as eluent provided 10.8 mg (17%) of N-[3-(3-chloro-phenyl)-1H-pyrazolo[3,4-d]thiazol-5-yl]-benzamide as a white solid. 1H NMR (d6-DMSO) δ: 13.70 and 13.72 (2 broad s, 1H, NH+tautomer), 12.9 (broad s, 1H, NH), 8.12 (d, 2H), 7.81 and 7.85 (2 broad s, 1H, tautomers), 7.65-7.74 (m, 2H), 7.54-7.62 (m, 3H), 7.45 (m, 1H); HPLC/MS m/z: 355 [MH]+.

Workup

  1. temperaturecooled at room temperature
  2. custompartitioned between ethyl acetate and sodium bicarbonate
  3. customThe organic layer was isolated
  4. customabsorbed on silica gel
  5. customPurification on silica gel with 0-10% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-03092cd8b82c4a9c84dd9d03925c78ec
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Reaction notes

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