Trifluoroacetic acid → (R)-2-[(RS)-2-amino-2-(6-bromo-pyridin-2-yl)-propoxy]-3,3,3-trifluoro-2-methyl-propionitrile

HRID 474055Notes

Reaction equation

HRID 474055 reaction equation
C(OC(=O)[NH:7][C:8]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[N:21]=1)([CH3:19])[CH2:9][O:10][C@@:11]([C:17]#[N:18])([CH3:16])[C:12]([F:15])([F:14])[F:13])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[N:21]=1)([CH3:19])[CH2:9][O:10][C@@:11]([CH3:16])([C:12]([F:13])([F:15])[F:14])[C:17]#[N:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86715548[(RS)-1-(6-Bromo-pyridin-2-yl)-2-((R)-1-cyano-2,2,2-trifluoro-1-methyl-ethoxy)-1-methyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 86668027(R)-2-[(RS)-2-amino-2-(6-bromo-pyridin-2-yl)-propoxy]-3,3,3-trifluoro-2-methyl-propionitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [(RS)-1-(6-bromo-pyridin-2-yl)-2-((R)-1-cyano-2,2,2-trifluoro-1-methyl-ethoxy)-1-methyl-ethyl]-carbamic acid tert-butyl ester (0.456 g, 1.008 mmol) and TFA (1.554 ml, 2.299 g, 20.17 mmol) in DCM (5 ml) was stirred at rt for 30 min, concentrated and triturated with 7N NH3/MeOH at rt for 20 min and again concentrated to give the title compound that was used for the next step without further purification. HPLC RtH4=0.69, 0.73 min (diastereomers); ESIMS: 352, 354 [(M+H)+].

Workup

  1. concentrationconcentrated
  2. customtriturated with 7N NH3/MeOH at rt for 20 min
  3. concentrationagain concentrated

Sources & evidence

ORD record
ord-058b6cadb3e040dfa1f5388f4b376f6d
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

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