Dimethyl Sulfoxide → HCID 178522522, compound

HRID 1452754Notes

Reaction equation

HRID 1452754 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].[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]([N:22]=[C:23]=[S:24])=[O:21].N1C=CC=CC=1.CS(C)=O>O>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:7]1[C:3]2[S:24][C:23]([NH:22][C:20]([C:16]3[O:15][CH:19]=[CH:18][CH:17]=3)=[O:21])=[N:14][C:4]=2[NH:5][N:6]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 27592432-Furoyl isothiocyanateHCID 178419699HCID 178419699, compound

Product 1

HCID 178522522HCID 178522522, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromo-5-pyridin-2-yl-2H-pyrazol-3-ylamine hydrobromide salt (193 mg, 0.60 mmol), furan-2-carbonyl isothiocyanate (0.07 mL), pyridine (0.1 mL), and DMSO (2 mL) was placed in a Smith process vial. The reaction was run in a Personal Chemistry SmithCreator microwave at 160° C. for five minutes. The reaction mixture was then added to an excess of water and the resulting precipitate was filtered. Purification by preparative HPLC afforded 10 mg of furan-2-carboxylic acid (3-pyridin-2-yl-1H-pyrazolo[3,4-d]thiazol-5-yl)-amide as a white solid. 1H-NMR (d6-DMSO) δ: 8.60 (dd, 1H), 7.92 (m, 2H), 7.80 (d, 1H), 7.46 (d, 1H), 7.26 (m, 2H), 6.60 (dd, 1H); HPLC/MS m/z: 312 [MH]+.

Workup

  1. filtrationthe resulting precipitate was filtered
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-1b0da44d088d4a729a7bf29b227b6cee
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Reaction notes

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