1-Hydroxybenzotriazole → HCID 59152105, compound
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]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:3]1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:56]1[N:60]2[CH:61]=[CH:62][CH:63]=[N:64][C:59]2=[C:58]([C:65](O)=[O:66])[CH:57]=1.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]([O:17][C:18]([F:21])([F:19])[F:20])=[CH:15][CH:16]=2)(=[O:10])=[O:9])[CH2:5][CH2:6][N:7]1[C:65]([C:58]1[CH:57]=[N:56][N:60]2[CH:61]=[CH:62][CH:63]=[N:64][C:59]=12)=[O:66]Participants
7
Reactant 5
HCID 757711-Hydroxybenzotriazole
HCID 81531Diisopropylethylamine
HCID 1910189Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid
HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 59152075(3S)-3-methyl-1-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazineProduct 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (3S)-3-methyl-1-({4-[(trifluoromethyl)oxy]phenyl}sulfonyl)piperazine (may be prepared as described in Description 13) (300 mg, 0.925 mmol), HOBt (142 mg, 0.925 mmol), HBTU (351 mg, 0.925 mmol) and pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (151 mg, 0.925 mmol) in DMF (50 ml) was added DIPEA (0.485 ml, 2.78 mmol) and the resulting mixture stirred at room temperature overnight, then concentrated under vacuum. The residue was redissolved in EtOAc, washed with aqueous NaHCO3 and brine, then concentrated under vacuum. Flash chromatography (silica; EtOAc) and concentration of the desired fractions gave the title compound (157 mg).
Workup
- concentrationconcentrated under vacuum
- dissolutionThe residue was redissolved in EtOAc
- washwashed with aqueous NaHCO3 and brine
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-3fc7bb913c684cdba6b229cd0db11533
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093249B2
Reaction notes
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