Ammonia → 4-((S)-4-{1-[(S)-6-(2-Hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-phenyl)-piperidine-1-carboxylic acid dimethylamide

HRID 80977Notes

Reaction equation

HRID 80977 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[OH:7][C:8]([CH3:38])([CH3:37])[CH2:9][C@@:10]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:15][C:14](=[O:16])[N:13]([C@H:17]([C:19]2[CH:24]=[CH:23][C:22]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:21][CH:20]=2)[CH3:18])[CH2:12][CH2:11]1.N1C=CC=CC=1.N>CN(C)C=O>[CH3:1][N:2]([CH3:6])[C:3]([N:28]1[CH2:29][CH2:30][CH:25]([C:22]2[CH:21]=[CH:20][C:19]([C@@H:17]([N:13]3[CH2:12][CH2:11][C@:10]([CH2:9][C:8]([OH:7])([CH3:37])[CH3:38])([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[O:15][C:14]3=[O:16])[CH3:18])=[CH:24][CH:23]=2)[CH2:26][CH2:27]1)=[O:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1049Pyridine2×HCID 6598Dimethylcarbamoyl Chloride2×HCID 58109308(S)-6-(2-Hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-piperidin-4-yl-phenyl)-ethyl]-[1,3]oxazinan-2-one

Product 1

HCID 451014134-((S)-4-{1-[(S)-6-(2-Hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-phenyl)-piperidine-1-carboxylic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethylcarbamoyl chloride (26 μL) was added to a solution of (S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-piperidin-4-yl-phenyl)-ethyl]-[1,3]oxazinan-2-one (120 mg) and pyridine (40 μL) in N,N-dimethylformamide (2 mL) at room temperature. The solution was stirred at room temperature for 5 h, before another portion of dimethylcarbamoyl chloride (26 μL) and pyridine (20 μL) were added. The solution was stirred at room temperature overnight. Then, diluted aqueous ammonia solution was added and the resulting mixture was concentrated under reduced pressure. The residue was purified by HPLC on reversed phase (MeOH/H2O/NH3) to afford the title compound.

Workup

  1. additionwere added
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. customThe residue was purified by HPLC on reversed phase (MeOH/H2O/NH3)

Sources & evidence

ORD record
ord-e7e0fe070fb84e2884fcaa7212d51d9b
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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