1-Hydroxybenzotriazole → HCID 59152107, compound

HRID 418308Notes

Reaction equation

HRID 418308 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][C:12]=2[CH3:21])(=[O:10])=[O:9])[CH2:3]1.[N:22]1[N:26]2[CH:27]=[CH:28][CH:29]=[N:30][C:25]2=[C:24]([C:31](O)=[O:32])[CH:23]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:1][C@H:2]1[CH2:3][N:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][C:12]=2[CH3:21])(=[O:9])=[O:10])[CH2:5][CH2:6][N:7]1[C:31]([C:24]1[CH:23]=[N:22][N:26]2[CH:27]=[CH:28][CH:29]=[N:30][C:25]=12)=[O:32]

Participants

7

Reactant 5

HCID 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 59152095HCID 59152095, compound

Product 1

HCID 59152107HCID 59152107, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3S)-3-methyl-1-{[2-methyl-4-(trifluoromethyl)phenyl]sulfonyl}piperazine (100 mg, 0.310 mmol) (may be prepared as described in Description 27), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (55.7 mg, 0.341 mmol), HOBt (52.3 mg, 0.341 mmol) and DIPEA (0.081 ml, 0.465 mmol) in dry DMF (5 ml) at rt was added HBTU (129 mg, 0.341 mmol) and the resulting orange solution stirred at rt for 45 min. Concentration under vacuum left an orange oil. Purification by MDAP and concentration of the desired fractions gave the title compound (108 mg) as a clear film that became a white solid on trituration with ether.

Workup

  1. concentrationConcentration under vacuum
  2. waitleft an orange oil
  3. customPurification by MDAP and concentration of the desired fractions

Sources & evidence

ORD record
ord-10a3848cd9d04c30bdb027d8b85d6056
Source dataset
uspto-grants-2012_01
Patent number
US08093249B2

Reaction notes

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