Triethylamine → HCID 59152110, compound

HRID 418304Notes

Reaction equation

HRID 418304 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].[F:20][C:21]1[CH:22]=[N:23][C:24]2[N:25]([N:27]=[CH:28][C:29]=2[C:30]([O-])=[O:31])[CH:26]=1.[Li+].C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH3:5][CH2:4][CH2:3][CH:2]([CH3:9])[CH3:1].[F:20][C:21]1[CH:22]=[N:23][C:24]2[N:25]([N:27]=[CH:28][C:29]=2[C:30]([N:16]2[CH2:17][CH2:18][N:13]([S:10]([C:9]3[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=3[CH3:1])(=[O:12])=[O:11])[CH2:14][C@@H:15]2[CH3:19])=[O:31])[CH:26]=1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 591520673-Methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrileHCID 66649478Lithium 6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 2

HCID 78922-MethylpentaneHCID 59152110HCID 59152110, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methyl-4-{[(3S)-3-methyl-1-piperazinyl]sulfonyl}benzonitrile (may be prepared as described in Description 9) (100 mg, 0.317 mmol), lithium 6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxylate (may be prepared as described in Description 16) (65.5 mg, 0.348 mmol), HOBT (58.2 mg, 0.380 mmol) and Et3N (0.110 ml, 0.792 mmol) in dry DMF (50 ml) at rt under Ar was added HBTU (144 mg, 0.380 mmol) and the resulting dark brown solution stirred at rt for 16 h. The mixture was concentrated under vacuum to leave a black oil. Purification by MDAP and concentration of the desired fractions gave a yellow film (109 mg). Flash chromatography (silica; Flash 12M; 3:1, EtOAc:isohexane) gave the title compound as a white foam (57.1 mg), that became a white solid on trituration with ether.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customto leave a black oil
  3. customPurification by MDAP and concentration of the desired fractions
  4. customgave a yellow film (109 mg)

Sources & evidence

ORD record
ord-3de6a90e580f4f1a951d0f07c50a0d77
Source dataset
uspto-grants-2012_01
Patent number
US08093249B2

Reaction notes

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