Water → 3-[((2S)-2-Methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]pyrazolo[1,5-a]pyrimidine

HRID 418295Notes

Reaction equation

HRID 418295 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3]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>[CH3:1][C@H:2]1[CH2:3][N:4]([S:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)(=[O:9])=[O:10])[CH2:5][CH2:6][N:7]1[C:30]([C:23]1[CH:22]=[N:21][N:25]2[CH:26]=[CH:27][CH:28]=[N:29][C:24]=12)=[O:31]

Participants

8

Reactant 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1910189Pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59152086(S)-3-Methyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperazine

Product 1

HCID 445957083-[((2S)-2-Methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}-1-piperazinyl)carbonyl]pyrazolo[1,5-a]pyrimidineYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3S)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared as described in Description 2) (80.0 mg, 0.259 mmol) in DMF (5 ml) was added pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (42.3 mg, 0.259 mmol), HOBT.H2O (39.7 mg, 0.259 mmol) and HBTU (98.0 mg, 0.259 mmol). Finally DIPEA (0.136 ml, 0.778 mmol) was added and the reaction mixture was stirred at room temperature for 3 hours. DMF was evaporated in vacuo then 5 ml of DCM added and washed with saturated aq. NaHCO3 solution (5 ml), dried on a phase separation cartridge and evaporated in vacuo. The crude material was dissolved in MeCN/DMSO 1:1 and purified by MDAP. The desired fractions were collected and concentrated in vacuo to give the title compound as a white solid (105 mg).

Workup

  1. customDMF was evaporated in vacuo
  2. addition5 ml of DCM added
  3. washwashed with saturated aq. NaHCO3 solution (5 ml)
  4. customdried on a phase separation cartridge
  5. customevaporated in vacuo
  6. dissolutionThe crude material was dissolved in MeCN/DMSO 1:1
  7. custompurified by MDAP
  8. customThe desired fractions were collected
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2e37a0e6f8b941209bee4f529b10a52c
Source dataset
uspto-grants-2012_01
Patent number
US08093249B2

Reaction notes

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