Ethyl 4-piperidinecarboxylate → HCID 68726962, compound

HRID 2067902Notes

Reaction equation

CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:15]2[N:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]([F:30])[F:29])=[CH:23][CH:22]=3)=[CH:17][N:16]=2)[CH:9]=1)(=O)=O.[NH:31]1[CH2:36][CH2:35][CH:34]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:33][CH2:32]1>CN(C=O)C>[F:30][CH:28]([F:29])[O:27][C:24]1[CH:25]=[CH:26][C:21]([C:18]2[CH:19]=[N:20][C:15]([NH:14][C:10]3[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=3)[CH2:7][CH2:6][N:31]3[CH2:36][CH2:35][CH:34]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:33][CH2:32]3)=[N:16][CH:17]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 95 °C

Procedure

3-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenethyl methanesulfonate 42b (0.7 mmol) and ethyl piperidine-4-carboxylate (1.7 mmol) are dissolved in DMF (6 mL) and heated to 95° C. for 6 h then cooled to rt. The reaction mixture is partitioned with EtOAc and water. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude material is purified by column chromatography on silica with hexane:EtOAc=1:1 to 100% EtOAc as eluant to yield ethyl 1-(3-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenethyl)piperidine-4-carboxylate 43 as clear crystalline solid. MS (m/z) (M+1)+: 497.2.

Workup

temperaturethen cooled to rt
customThe reaction mixture is partitioned with EtOAc and water
washThe organic layer is washed with water, brine
dry with materialdried over magnesium sulfate
filtrationfiltered
customThe crude material is purified by column chromatography on silica with hexane

Sources & evidence

ORD record: ord-00bfa8481d15429e8ffe81d871dc31f5
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293757B2

Reaction notes

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