Ethyl 4-piperidinecarboxylate → HCID 68726041, compound

HRID 2067912Notes

Reaction equation

HRID 2067912 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([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:11]=[CH:10][C:9]=1[CH3:31])(=O)=O.[NH:32]1[CH2:37][CH2:36][CH:35]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:34][CH2:33]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:12]3[CH:11]=[CH:10][C:9]([CH3:31])=[C:8]([CH:13]=3)[CH2:7][CH2:6][N:32]3[CH2:37][CH2:36][CH:35]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:34][CH2:33]3)=[N:16][CH:17]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 86660124HCID 86660124, compound

Product 1

HCID 68726041HCID 68726041, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

5-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-methylphenethyl methanesulfonate 51b (0.9 mmol), ethyl piperidine-4-carboxylate (2.2 mmol) are dissolved in DMF (10 mL) and heated to 90° C. for 4 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-(5-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-methylphenethyl)piperidine-4-carboxylate 52 as clear viscous oil. MS (m/z) (M+1)+: 511.2.

Workup

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

Sources & evidence

ORD record
ord-1e5da6b067bb4cacbcff4f9b76c3f17b
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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