Diisopropylethylamine → Ammonia

HRID 418299Notes

Reaction equation

HRID 418299 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10]([N:13]1[CH2:18][CH2:17][NH:16][C@@H:15]([CH3:19])[CH2:14]1)(=[O:12])=[O:11])[C:5]#[N:6].[N:20]1[N:24]2[CH:25]=[CH:26][CH:27]=[N:28][C:23]2=[C:22]([C:29](O)=[O:30])[CH:21]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CO.C(Cl)Cl>[NH3:6].[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10]([N:13]1[CH2:18][CH2:17][N:16]([C:29]([C:22]2[CH:21]=[N:20][N:24]3[CH:25]=[CH:26][CH:27]=[N:28][C:23]=23)=[O:30])[C@@H:15]([CH3:19])[CH2:14]1)(=[O:12])=[O:11])[C:5]#[N:6]

Participants

9

Reactant 4

HCID 81531DiisopropylethylamineHCID 1910189Pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 591520673-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile

Product 2

HCID 222AmmoniaHCID 59152092HCID 59152092, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile (may be prepared as described in Description 9) (75 mg, 0.268 mmol), pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (48.2 mg, 0.295 mmol) and DIPEA (0.070 ml, 0.403 mmol) in dry DMF (3 ml) at rt under argon was added HATU (122 mg, 0.322 mmol) and the resulting yellow solution stirred at rt for 1 hour. Concentration in vacuo gave a yellow oil, that was purified by MDAP; concentration of the desired fractions gave a clear film (80.2 mg). Flash chromatography (silica; Flash 12S; linear gradient (1-8%) [2M NH3 in MeOH] in DCM) gave the title compound as a clear film (44.9 mg), that became a white solid on standing in vacuo (1 mbar) for 1 h.

Workup

  1. concentrationConcentration in vacuo
  2. customgave a yellow oil, that
  3. customwas purified by MDAP
  4. customconcentration of the desired fractions gave a clear film (80.2 mg)

Sources & evidence

ORD record
ord-3fb47c3eb07a420e9b28416c87579ac5
Source dataset
uspto-grants-2012_01
Patent number
US08093249B2

Reaction notes

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