Trifluoroacetic acid → HCID 59394561, compound

HRID 45121Notes

Reaction equation

HRID 45121 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([S:44]([CH3:47])(=[O:46])=[O:45])[CH2:14][C:15]2[CH:20]=[C:19]([O:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31](=[O:43])[NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=3)[CH:26]=[CH:25]4)[N:18]=[CH:17][N:16]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:42][C:39]([F:40])([F:41])[C:35]1[CH:34]=[C:33]([NH:32][C:31]([N:27]2[C:28]3[C:24](=[CH:23][C:22]([O:21][C:19]4[CH:20]=[C:15]([CH2:14][N:13]([S:44]([CH3:47])(=[O:46])=[O:45])[CH:10]5[CH2:11][CH2:12][NH:8][CH2:9]5)[N:16]=[CH:17][N:18]=4)=[CH:30][CH:29]=3)[CH:25]=[CH:26]2)=[O:43])[CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59394231HCID 59394231, compound

Product 1

HCID 59394561HCID 59394561, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±)-3-(Methanesulfonyl-{6-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl}-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester (12 mg, 0.018 mmol) is stirred in a solution of DCM (2 mL) and TFA (0.5 mL) overnight. After removal of solvents, the residue is quenched with saturated aqueous sodium bicarbonate. The mixture is extracted with EtOAc (3×). The combined organic layers are washed with water and brine and the organic layer is dried with Na2SO4, filtered, and condensed. The residue is then separated by FCC (0-10%, 2 M NH3 in MeOH/DCM) to provide the title compound. MS (ESI) m/z 574.8 (M+1).

Workup

  1. customAfter removal of solvents
  2. customthe residue is quenched with saturated aqueous sodium bicarbonate
  3. extractionThe mixture is extracted with EtOAc (3×)
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialthe organic layer is dried with Na2SO4
  6. filtrationfiltered
  7. customcondensed
  8. customThe residue is then separated by FCC (0-10%, 2 M NH3 in MeOH/DCM)

Sources & evidence

ORD record
ord-ead6abe8ce7040788e4a7be991828a0c
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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