Diisopropylethylamine → 6-acetyl-N-(3-(3,3-dimethyl-2-oxopyrrolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamide

HRID 632800Notes

Reaction equation

HRID 632800 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.[C:17]([C:20]1[N:25]=[C:24]([C:26](O)=[O:27])[CH:23]=[CH:22][CH:21]=1)(=[O:19])[CH3:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C.C(OCC)(=O)C.O>[C:17]([C:20]1[N:25]=[C:24]([C:26]([NH:2][C:3]2[C:4]([N:9]3[CH2:13][CH2:12][C:11]([CH3:14])([CH3:15])[C:10]3=[O:16])=[N:5][N:6]([CH3:8])[CH:7]=2)=[O:27])[CH:23]=[CH:22][CH:21]=1)(=[O:19])[CH3:18]

Participants

8

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 152065046-Acetylpicolinic acidHCID 1180609051-(4-amino-1-methyl-1H-pyrazol-3-yl)-3,3-dimethylpyrrolidin-2-one hydrochloride

Product 1

HCID 1180613906-acetyl-N-(3-(3,3-dimethyl-2-oxopyrrolidin-1-yl)-1-methyl-1H-pyrazol-4-yl)pyridine-2-carboxamideYield 101.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(4-amino-1-methyl-1H-pyrazol-3-yl)-3,3-dimethylpyrrolidin-2-one hydrochloride (50 mg), 6-acetylpyridine-2-carboxylic acid (37 mg) and HATU (101 mg) in DMF (3.0 mL) was added ethyldiisopropylamine (71 μL) at room temperature, and the mixture was stirred for 20 hr. The reaction mixture was diluted with ethyl acetate, and water was added thereto. The extract was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (74 mg).

Workup

  1. additionwas added
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-775186bf85854e59a2276ba15acfe1e6
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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