Water → HCID 59509049, compound

HRID 1020066Notes

Reaction equation

HRID 1020066 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH2:16])[CH:10]=1.[CH2:17]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH2:30][CH:29]([C:33](Cl)=[O:34])[CH2:28]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>ClCCl.CN(C1C=CN=CC=1)C>[CH2:17]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH2:30][CH:29]([C:33](=[O:34])[NH:16][C:11]2[CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N:14]=[C:13]([CH3:15])[N:12]=2)[CH2:28]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 962WaterHCID 2776575benzyl 3-(chlorocarbonyl)tetrahydro-1(2H)-pyridinecarboxylateHCID 45788190HCID 45788190, compound

Product 1

HCID 59509049HCID 59509049, compoundYield 114.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

6-(2-Methoxy-phenyl)-2-methyl-pyrimidin-4-ylamine (XXXVI) (0.111 g, 0.512 mmol) was taken in 3 ml of dry dichloromethane, DMAP (0.075 g, 0.614 mmol) and a solution of 3-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester (XXV) (0.155 g, 0.563 mmol) in dichloromethane (1 ml) were added dropwise at room temperature and the reaction mixture was stirred for 3 hours. Then water was added to the reaction mixture followed by extraction with dichloromethane. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to provide 0.270 g of 3-[6-(2-methoxy-phenyl)-2-methyl-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XXXVII).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d811b6ec49148798853deee1528e02b
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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