N-Methylbenzylamine → HCID 22452596, compound

HRID 2185837Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([C:11]2[CH:12]=[C:13]([C:28]#[N:29])[C:14](=[O:27])[NH:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.C[NH:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[C:39](OCC)(=O)C>>[O:27]=[C:14]1[C:13]([C:28]#[N:29])=[CH:12][C:11]([C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH:31][CH:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH3:39])[N:10]=2)=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[NH:15]1

Participants

Reactant 3

HCID 7669N-Methylbenzylamine

HCID 8857Ethyl Acetate

HCID 15541009HCID 15541009, compound

Product 1

HCID 22452596HCID 22452596, compoundYield 73%

Conditions

Temperature: 100 °C

Procedure

To 5-(2-methylsulfonylpyrimidin-4-yl)-2-oxo-6-(3-trifluoromethylphenyl)-1,2-dihydropyridine-3-carbonitrile (150 mg, 0.357 mmol) in a sealed tube was added (S)-∝-methylbenzylamine (150 mg) and the mixture heated under argon at 100° C. for 1 hour. The reaction was cooled and the oil dissolved in ethyl acetate (25 mL). The solution was washed 3 times with a pH 5.3 buffer solution of 10% citric acid/NaOH (15 mL). The ethyl acetate layer was dried over sodium sulfate concentrated and chromatographed on silica using 80% ethyl acetate/hexane to give 120 mg (73%) of the title compound as a solid. The solid was stirred in methanol/hexane (2 mL) for 1 hour, filtered, and dried 40° C. to give 105 mg of a solid.

Workup

temperatureThe reaction was cooled
washThe solution was washed 3 times with a pH 5.3 buffer solution of 10% citric acid/NaOH (15 mL)
dry with materialThe ethyl acetate layer was dried over sodium sulfate
concentrationconcentrated
customchromatographed on silica using 80% ethyl acetate/hexane

Sources & evidence

ORD record: ord-3d5a1a1d25b747a4ade895f0cfc48f2b
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06403596B1

Reaction notes

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