Trifluoroacetic acid → HCID 58972425, compound

HRID 2264511Notes

Reaction equation

HRID 2264511 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[N:24])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]2[N:16]=[CH:17][C:18]([O:21][CH2:22][C:23]#[N:24])=[CH:19][N:20]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68779156HCID 68779156, compound

Product 1

HCID 58972425HCID 58972425, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(5-cyanomethoxy-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.67 g, 2.0 mmol, 1.0 equiv) in dichloromethane (15 mL) was added drop by drop 90% trifluoroacetic acid (1.82 mL, 2.55 g, 20 mmol, 10 equiv) and the reaction was stirred at rt for 16 h. The reaction mixture was evaporated and the residue partitioned between water and dichloromethane. The pH of the water phase was adjusted to 9-10 by addition of a sat. solution of potassium carbonate and the mixture extracted three times with dichloromethane. The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated by evaporation under reduced pressure. The crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol (+25% ammonia in water) to give 0.32 g (69%) of the title compound as colorless oil. MS (ISP): 234.0 [M+H]+.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue partitioned between water and dichloromethane
  3. additionThe pH of the water phase was adjusted to 9-10 by addition of a sat. solution of potassium carbonate
  4. extractionthe mixture extracted three times with dichloromethane
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe crude product was purified by column chromatography on silica eluting with a gradient of dichloromethane/methanol (+25% ammonia in water)

Sources & evidence

ORD record
ord-6df4074e80044482811af1673d6cd8d7
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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