(S)-tert-butyl (1-(3-bromo-6-(3-hydroxy-3-methylazetidin-1-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate → (S)-1-(6-(1-amino-2-(3,5-difluorophenyl)ethyl)-5-bromopyridin-2-yl)-3-methylazetidin-3-ol

HRID 2170378Notes

Reaction equation

HRID 2170378 reaction equation
[Br:1][C:2]1[C:3]([C@@H:14]([NH:24]C(=O)OC(C)(C)C)[CH2:15][C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=2)=[N:4][C:5]([N:8]2[CH2:11][C:10]([OH:13])([CH3:12])[CH2:9]2)=[CH:6][CH:7]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:24][C@H:14]([C:3]1[N:4]=[C:5]([N:8]2[CH2:11][C:10]([CH3:12])([OH:13])[CH2:9]2)[CH:6]=[CH:7][C:2]=1[Br:1])[CH2:15][C:16]1[CH:17]=[C:18]([F:23])[CH:19]=[C:20]([F:22])[CH:21]=1

Participants

3

Reactant 1

HCID 90290192(S)-tert-butyl (1-(3-bromo-6-(3-hydroxy-3-methylazetidin-1-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

Product 1

HCID 90280371(S)-1-(6-(1-amino-2-(3,5-difluorophenyl)ethyl)-5-bromopyridin-2-yl)-3-methylazetidin-3-ol

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Compound 42G (64 mg, 0.13 mmol) was dissolved in 2 mL of 20% TFA/methylene chloride. The reaction mixture was stirred at room temperature for 2 hours and then partitioned between EtOAc and saturated aq. NaHCO3. The organic layer was separated and concentrated to afford the title product. MS (m/z) 398.03[M+H]+.

Workup

  1. custompartitioned between EtOAc and saturated aq. NaHCO3
  2. customThe organic layer was separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fbc759cea6254b63a98e9cc4f783b827
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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