Benzenesulfonamide → HCID 58063231, compound

HRID 474346Notes

Reaction equation

HRID 474346 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[C:4]2[N:3]=1.[C:17]1([S:23]([NH2:26])(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[CH:14]([NH:13][C:11]([C:10]1[CH:9]=[N:8][N:5]2[CH:6]=[CH:7][C:2]([NH:26][S:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:25])=[O:24])=[N:3][C:4]=12)=[O:12])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 10796Cesium carbonateHCID 58063476HCID 58063476, compound

Product 1

HCID 58063231HCID 58063231, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-chloro-N-isopropylpyrazolo[1,5-a]pyrimidine-3-carboxamide (95.5 mg, 0.40 mmol, 1.0 equiv), benzenesulfonamide (62.0 mg, 0.40 mmol, 1.0 equiv) and cesium carbonate (312 mg, 0.96 mmol, 2.4 equiv) in 1,2-dimethoxyethane (8 mL) was heated to 85° C. for 72 hours. The solvent was removed in vacuo, and the resultant residue dissolved in water. The pH of the solution was then adjusted to about 5 by the addition of 1M HCl aqueous solution and extracted with dichloromethane (2×30 mL). The organic extracts were concentrated under vacuum and the residue purified by flash column chromatography on silica gel (gradient: 0 to 10% methanol in dichloromethane) to afford 57.0 mg (40%) of 5-benzenesulfonylamino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid isopropylamide as a solid. LCMS (ESI) m+H=360.3; 1H NMR (400 MHz, DMSO-d6) δ: 12.2 (s, 1H), 8.97 (d, 1H), 8.30 (s, 1H), 8.01 (d, 2H), 7.64 (m, 4H), 6.64 (m, 1H), 4.13 (m, 1H), 1.21 (d, 6H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe resultant residue dissolved in water
  3. additionThe pH of the solution was then adjusted to about 5 by the addition of 1M HCl aqueous solution
  4. extractionextracted with dichloromethane (2×30 mL)
  5. concentrationThe organic extracts were concentrated under vacuum
  6. customthe residue purified by flash column chromatography on silica gel (gradient: 0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-275d60baaf6646d4994dfb4ed56db803
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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