Piperidine → HCID 11712354, compound

HRID 883010Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:36]=[CH:37][CH:38]=1)[CH2:12][N:13]([CH:33]([CH3:35])[CH3:34])[C:14]([C:16]1[C:17]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])=[N:18][C:19](S(C)(=O)=O)=[N:20][CH:21]=1)=[O:15]>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:36]=[CH:37][CH:38]=1)[CH2:12][N:13]([CH:33]([CH3:35])[CH3:34])[C:14]([C:16]1[C:17]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])=[N:18][C:19]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:20][CH:21]=1)=[O:15]

Participants

Conditions

Temperature: 80 °C

Procedure

Piperidine (0.0054 g, 0.064 mmol) was added to a stirred solution of N-(3-methoxybenzyl)-4-(2-fluorophenyl)-N-isopropyl-2-(methylsulfonyl)pyrimidine-5-carboxamide (0.015 g, 0.032 mmol) in THF (1 mL) and the mixture was heated at 80° C. for 1 h. The solvent was removed under reduced pressure, and the product was purified by preparative HPLC (5-80% CH3CN/0.05% TFA gradient over 15 min) to give N-(3-methoxybenzyl)-4-(2-fluorophenyl)-N-isopropyl-2-(piperdin-1-yl)pyrimidine-5-carboxamide Compound No. 20 (0.012 g, 81%).

Workup

customThe solvent was removed under reduced pressure
customthe product was purified by preparative HPLC (5-80% CH3CN/0.05% TFA gradient over 15 min)

Sources & evidence

ORD record: ord-ea89ca548a8a4ad0b9dbb81f746b6f42
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236815B2

Reaction notes

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