Trifluoroacetic acid → HCID 73297208, compound

HRID 592418Notes

Reaction equation

HRID 592418 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:47])[CH:10]([C:12]1[CH:46]=[CH:45][CH:44]=[CH:43][C:13]=1[CH2:14][CH2:15][C:16]1[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([CH:30]3[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]3)=[N:28][CH:29]=2)[N:17]=1)[CH3:11]>C(Cl)Cl>[Cl:22][C:21]1[C:16]([CH2:15][CH2:14][C:13]2[CH:43]=[CH:44][CH:45]=[CH:46][C:12]=2[CH:10]([CH3:11])[C:9]([NH2:8])=[O:47])=[N:17][C:18]([NH:23][C:24]2[CH:29]=[N:28][C:27]([CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)=[CH:26][CH:25]=2)=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712308HCID 86712308, compound

Product 1

HCID 73297208HCID 73297208, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.71 mL) was added to a solution of tert-butyl 4-(5-((4-(2-(1-amino-1-oxopropan-2-yl)phenethyl)-5-chloropyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate A31 (34 mg, 0.06 mmol) in DCM (7 mL) and the mixture was stirred at room temperature overnight. The volatiles were removed in vacuo before the addition of 2.0 M NaOH solution (2 mL) and EtOAc. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with water, dried over Na2SO4 and the solvent removed under reduced pressure to give the title compound 37 (23 mg, 82%). LCMS-C: rt 6.02 min; m/z 465.3 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo before the addition of 2.0 M NaOH solution (2 mL) and EtOAc
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a68e1b11ff0343d2974c72c93025b36a
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

Loading…