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

HRID 538316Notes

Reaction equation

HRID 538316 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-4b078c427abb4f0f9c94bc6f7279e60b
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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