Diisopropylethylamine → N-(3-(3,3-dimethyl-2-oxopyrrolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)-3-(1,3-thiazol-2-ylsulfonyl)benzamide

HRID 632793Notes

Reaction equation

HRID 632793 reaction equation
Cl.[NH2:2][C:3]1[C:4]([N:9]2[CH2:13][CH2:12][C:11]([CH3:15])([CH3:14])[C:10]2=[O:16])=[N:5][N:6]([CH3:8])[CH:7]=1.[S:17]1[CH:21]=[CH:20][N:19]=[C:18]1[S:22]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](O)=[O:29])(=[O:24])=[O:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[CH3:15][C:11]1([CH3:14])[CH2:12][CH2:13][N:9]([C:4]2[C:3]([NH:2][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][CH:33]=[C:25]([S:22]([C:18]4[S:17][CH:21]=[CH:20][N:19]=4)(=[O:24])=[O:23])[CH:26]=3)=[CH:7][N:6]([CH3:8])[N:5]=2)[C:10]1=[O:16]

Participants

7

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 1180609051-(4-amino-1-methyl-1H-pyrazol-3-yl)-3,3-dimethylpyrrolidin-2-one hydrochlorideHCID 1180610983-(2-Thiazolylsulfonyl)benzoic acid

Product 1

HCID 118061070N-(3-(3,3-dimethyl-2-oxopyrrolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)-3-(1,3-thiazol-2-ylsulfonyl)benzamideYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-amino-1-methyl-1H-pyrazol-3-yl)-3,3-dimethylpyrrolidin-2-one hydrochloride (30 mg) and 3-(1,3-thiazol-2-ylsulfonyl)benzoic acid (33.0 mg) in DMF (0.61 mL) were added HATU (56 mg) and diisopropylethylamine (43 μL). The reaction mixture was stirred overnight at room temperature, and poured into water, and the precipitate was collected by filtration, purified by silica gel column chromatography (NH, ethyl acetate/hexane), and recrystallized from ethyl acetate/hexane to give the title compound (40 mg).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. custompurified by silica gel column chromatography (NH, ethyl acetate/hexane)
  3. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-679efddcded8410dba8709369bddfa50
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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