Water → 3-{[4-({4-[(Trifluoromethyl)oxy]phenyl}sulfonyl)-1-piperazinyl]carbonyl}pyrazolo[1,5-a]pyrimidine

HRID 418302Notes

Reaction equation

HRID 418302 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.[N:21]1[N:25]2[CH:26]=[CH:27][CH:28]=[N:29][C:24]2=[C:23]([C:30](O)=[O:31])[CH:22]=1.C1C=CC2N(O)N=NC=2C=1.O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:20][C:2]([F:1])([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[CH2:14][CH2:15][N:16]([C:30]([C:23]3[CH:22]=[N:21][N:25]4[CH:26]=[CH:27][CH:28]=[N:29][C:24]=34)=[O:31])[CH2:17][CH2:18]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

8

Reactant 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1910189Pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 20794021-[4-(Trifluoromethoxy)benzenesulfonyl]piperazineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 591521013-{[4-({4-[(Trifluoromethyl)oxy]phenyl}sulfonyl)-1-piperazinyl]carbonyl}pyrazolo[1,5-a]pyrimidineYield 69.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazine (may be prepared as described in Description 11) (300 mg, 0.967 mmol) in DMF (15 ml) was added pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (158 mg, 0.967 mmol), HOBT.H2O (148 mg, 0.967 mmol) and HBTU (368 mg, 0.967 mmol). Finally DIPEA (0.507 ml, 2.90 mmol) was added and the reaction mixture was stirred at rt for 20 hours. Solvent was removed by evaporation, the crude material partitioned between DCM (50 ml) and saturated sodium bicarbonate (50 ml), the DCM layer collected, washed with 2N HCl aq. (50 ml), dried (hydrophobic frit) and evaporated. The crude was purified by MDAP. MDAP fractions were evaporated and the crude material partitioned between DCM (20 ml) and sat. sodium bicarbonate solution (20 ml). The DCM layer was collected and dried (hydrophobic frit) and evaporated to give the title compound (308 mg).

Workup

  1. customSolvent was removed by evaporation
  2. customthe crude material partitioned between DCM (50 ml) and saturated sodium bicarbonate (50 ml)
  3. customthe DCM layer collected
  4. washwashed with 2N HCl aq. (50 ml)
  5. customdried (hydrophobic frit)
  6. customevaporated
  7. customThe crude was purified by MDAP
  8. customMDAP fractions were evaporated
  9. customthe crude material partitioned between DCM (20 ml) and sat. sodium bicarbonate solution (20 ml)
  10. customThe DCM layer was collected
  11. customdried (hydrophobic frit)
  12. customevaporated

Sources & evidence

ORD record
ord-ebb58df187734f19a204b7af31293d42
Source dataset
uspto-grants-2012_01
Patent number
US08093249B2

Reaction notes

Loading…