N-Methyl-2-piperidone → HCID 66703723, compound

HRID 426011Notes

Reaction equation

HRID 426011 reaction equation
F[C:2]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:18])[N:14]2[CH3:17])=[CH:9][CH:8]=1)=[O:5].CN1CCCCC1=O.[NH2:35][C@@H:36]([CH3:39])[CH2:37][OH:38]>>[OH:38][CH2:37][C@@H:36]([NH:35][C:2]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:18])[N:14]2[CH3:17])=[CH:9][CH:8]=1)=[O:5])[CH3:39]

Participants

4

Reactant 3

HCID 13603N-Methyl-2-piperidoneHCID 80307L-AlaninolHCID 667036052-fluoro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-(trifluoromethyl)benzamide

Product 1

HCID 66703723HCID 66703723, compoundYield 65.4%

Conditions

Temperature
180 °C

Procedure

2-Fluoro-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-(trifluoromethyl)benzamide (250 mg), N-methylpiperidone (0.5 mL) and (2S)-2-aminopropan-1-ol (800 mg) were mixed, followed by stirring at 180° C. for 40 minutes under microwave irradiation. After spontaneous cooling and subsequent purification by silica gel column chromatography (chloroform:methanol, 99:1 to 95:5), 2-{[(1S)-2-hydroxy-1-methylethyl]amino}-N-(1-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)-4-(trifluoromethyl)benzamide (188 mg) was obtained as a solid.

Workup

  1. temperatureAfter spontaneous cooling
  2. customsubsequent purification by silica gel column chromatography (chloroform:methanol, 99:1 to 95:5)

Sources & evidence

ORD record
ord-43b19f486fa8451db8f3e66a00599959
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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