Diisopropylethylamine → HCID 66649655, compound

HRID 418306Notes

Reaction equation

HRID 418306 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([OH:13])=O)[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:38][C@@H:39]1[NH:44][CH2:43][CH2:42][N:41]([S:45]([C:48]2[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=2)(=[O:47])=[O:46])[CH2:40]1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([N:44]2[CH2:43][CH2:42][N:41]([S:45]([C:48]3[CH:49]=[CH:50][C:51]([C:54]([F:57])([F:55])[F:56])=[CH:52][CH:53]=3)(=[O:46])=[O:47])[CH2:40][C@@H:39]2[CH3:38])=[O:13])[CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 252207936-Bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 59152086(S)-3-Methyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)piperazine

Product 1

HCID 66649655HCID 66649655, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromopyrazolo[1,5-a]pyrimidine-3-carboxylic acid (may be prepared as described in Description 17) (471 mg, 1.946 mmol) in N,N-Dimethylformamide (10 mL) under a flush of argon was added HATU (740 mg, 1.946 mmol) and the reaction stirred for 10 minutes. (3S)-3-methyl-1-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared as described in Description 2) (600 mg, 1.946 mmol) was then added followed by N,N-diisopropylethylamine (0.680 mL, 3.89 mmol) and the reaction stirred for 18 h. The reaction mixture was partitioned between ethyl acetate (60 mL) and water (40 mL). The organic layer was washed with further water (20 mL) and brine (20 mL) before it was dried (MgSO4), filtered and the solvent removed in vacuo. The crude material was purified by silica chromatography, 40 M cartridge, eluting 0-75% EtOAC in isohexane and the solvent evaporated to give the title compound (587 mg) as a white solid.

Workup

  1. stirringthe reaction stirred for 18 h
  2. customThe reaction mixture was partitioned between ethyl acetate (60 mL) and water (40 mL)
  3. washThe organic layer was washed with further water (20 mL) and brine (20 mL) before it
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe crude material was purified by silica chromatography, 40 M cartridge
  8. washeluting 0-75% EtOAC in isohexane
  9. customthe solvent evaporated

Sources & evidence

ORD record
ord-d084363366a546a297c61206917c2ac2
Source dataset
uspto-grants-2012_01
Patent number
US08093249B2

Reaction notes

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