Ethyl 4-piperidinecarboxylate → HCID 68728956, compound

HRID 2067900Notes

Reaction equation

HRID 2067900 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]2[N:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]([F:31])[F:30])=[CH:24][CH:23]=3)=[CH:18][N:17]=2)[CH:10]=1)(=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:31][CH:29]([F:30])[O:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]2[CH:20]=[N:21][C:16]([NH:15][C:11]3[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=3)[O:8][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:17][CH:18]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 86660120HCID 86660120, compound

Product 1

HCID 68728956HCID 68728956, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

2-(3-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenoxy)ethyl methanesulfonate 40b (0.4 mmol), ethyl piperidine-4-carboxylate (0.9 mmol) are dissolved in DMF (3 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 product is triturated with MeOH and filtered to yield ethyl 1-(2-(3-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenoxy)ethyl)piperidine-4-carboxylate 41 as white solid. MS (m/z) (M+1)+: 513.2.

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 product is triturated with MeOH
  7. filtrationfiltered

Sources & evidence

ORD record
ord-b7943aac52694a1987bd9a08e200c5d7
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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