Pyridine → HCID 178522521, compound

HRID 1452750Notes

Reaction equation

HRID 1452750 reaction equation
Br.Br[C:3]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:6][NH:5][C:4]=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.N1C=CC=CC=1.O1CCOCC1>O.CS(C)=O>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[C:3]2[S:25][C:24]([NH:23][C:15](=[O:22])[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:14][C:4]=2[NH:5][N:6]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 312751,4-DioxaneHCID 68284Benzoyl isothiocyanateHCID 178419699HCID 178419699, compound

Product 1

HCID 178522521HCID 178522521, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 4-bromo-5-pyridin-2-yl-2H-pyrazol-3-ylamine hydrobromide salt (300 mg, 0.94 mmol), benzoyl isothiocyanate (0.15 mL, 1.12 mmol), pyridine (0.24 mL, 2.97 mmol), 1,4-dioxane (2 mL), and DMSO (2 mL) was heated at 95° C. overnight. The mixture was added to an excess of water, and the resulting precipitate was filtered, and recrystallized from EtOH to afford 190 mg (63%) of N-(3-pyridin-2-yl-1H-pyrazolo[3,4-d]thiazol-5-yl)-benzamide as an off-white solid. 1H NMR (d6-DMSO) δ: 8.85 (s, 1H), 8.02 (m, 4H), 7.51 (m, 3H), 7.21 (m, 1H); HPLC/MS m/z: 322 [MH]+.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-28824c4a6e804ff9b3784bcc60018370
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Reaction notes

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