Water → HCID 53884725, compound

HRID 650631Notes

Reaction equation

HRID 650631 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH3:28])[C:8]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:12][C:13]([CH2:16]OS(C)(=O)=O)=[N:14][CH:15]=1)=[O:9].[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.O>C(Cl)Cl>[F:1][C:2]([F:36])([F:37])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:34])([F:33])[F:35])[CH:31]=1)[CH2:6][N:7]([CH3:28])[C:8]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:12][C:13]([CH2:16][N:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[N:14][CH:15]=1)=[O:9]

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 54354681HCID 54354681, compound

Product 1

HCID 53884725HCID 53884725, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.40 g (0.73 mmol) methanesulfonic acid 5-[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-4-phenyl-pyrimidin-2-ylmethyl ester in 5 ml CH2Cl2 added 0.11 ml (1.1 mmol) piperidine were added. The reaction mixture was stirred for 16 hrs. at RT and than poured into H2O and extracted three times with 50 ml CH2Cl2. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2/MeOH 10:1) to give 0.32 g (81%) 4-phenyl-2-piperidin-1-ylmethyl-pyrimidine-5-carboxylic acid (3,5-bis-trifluoromethyl-benzyl)-methyl-amide as a pale yellow waxy solid, MS (ISP): 537.2 (M+H+).

Workup

  1. additionwere added
  2. extractionextracted three times with 50 ml CH2Cl2
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography (SiO2, CH2Cl2/MeOH 10:1)

Sources & evidence

ORD record
ord-6fb657b3b78c41f2ba88c239c4af4603
Source dataset
uspto-grants-2001_08
Patent number
US06274588B1

Reaction notes

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