Hydrochloric Acid → 2-[3,5-Bis(trifluoromethyl)phenyl]-n{4-(2-chloro-4-fluorophenyl)-6-[(7s,9as)-7-(hydroxymethyl)hexahydropyrazino[2,1-c][1,4]oxazin-8(1h)-yl]-3-pyridinyl}-n,2-dimethylpropanamide

HRID 2245489Notes

Reaction equation

HRID 2245489 reaction equation
[F:1][C:2]([F:54])([F:53])[C:3]1[CH:4]=[C:5]([C:13]([CH3:52])([CH3:51])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[C@H:41]([CH2:42][O:43][Si](C(C)(C)C)(C)C)[CH2:40][N:39]4[C@H:34]([CH2:35][O:36][CH2:37][CH2:38]4)[CH2:33]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[Cl:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl>CO>[F:54][C:2]([F:1])([F:53])[C:3]1[CH:4]=[C:5]([C:13]([CH3:52])([CH3:51])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[C@H:41]([CH2:42][OH:43])[CH2:40][N:39]4[C@H:34]([CH2:35][O:36][CH2:37][CH2:38]4)[CH2:33]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[Cl:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 592158392-[3,5-bis(trifluoromethyl)phenyl]-N-(4-(2-chloro-4-fluorophenyl)-6-[(7S,9aS)-7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]-3-pyridinyl}-N,2-dimethylpropanamide

Product 1

HCID 160639492-[3,5-Bis(trifluoromethyl)phenyl]-n{4-(2-chloro-4-fluorophenyl)-6-[(7s,9as)-7-(hydroxymethyl)hexahydropyrazino[2,1-c][1,4]oxazin-8(1h)-yl]-3-pyridinyl}-n,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2-[3,5-bis(trifluoromethyl)phenyl]-N-{4-(2-chloro-4-fluorophenyl)-6-[(7S,9aS)-7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)hexahydropyrazino[2,1-c][1,4]oxazin -8(1H)-yl]-3-pyridinyl}-N,2-dimethylpropanamide (D58, 22 mg, 0.027 mmol) was dissolved in dry MeOH (2 mL), cooled in an ice-salt bath to ˜0° C. before adding c.HCl solution (˜0.1 mL), slowly. The reaction mixture was stirred at ˜0° C. for 1 hour before warming up and stirring at R.T. for 2 hours. Placed directly onto a 2 g SCX column, washing with MeOH (2×5 mL) before eluting the compound off with NH3 in MeOH (4×5 mL). Solvent evaporated under reduced pressure to afford the title compound as an off white solid. (10mg)

Workup

  1. additionbefore adding c
  2. temperaturebefore warming up
  3. stirringstirring at R.T. for 2 hours
  4. washwashing with MeOH (2×5 mL)
  5. washbefore eluting the compound off with NH3 in MeOH (4×5 mL)
  6. customSolvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-ea4225d8229f46f7bf9e21f77680110d
Source dataset
uspto-grants-2010_03
Patent number
US07683056B2

Reaction notes

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