CID 6432229 → 2-[3,5-Bis(trifluoromethyl)phenyl]-n{4-(5-fluoro-2-methylphenyl)-6-[(7s,9as)-7-(hydroxymethyl)hexahydropyrazino[2,1-c][1,4]oxazin-8(1h)-yl]-3-pyridinyl}-n,2-dimethylpropanamide

HRID 2074917Notes

Reaction equation

HRID 2074917 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]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH]Cl>CO>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[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]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:54])[F:53])[CH:8]=1

Participants

4

Reactant 2

HCID 6432229CID 6432229HCID 592158952-[3,5-bis(trifluoromethyl)phenyl]-N-[6-[(7S,9aS)-7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]-4-(5-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide

Product 1

HCID 160639132-[3,5-Bis(trifluoromethyl)phenyl]-n{4-(5-fluoro-2-methylphenyl)-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

Procedure

2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-[(7S,9aS)-7-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)hexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl]-4-(5-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide (D56, 110 mg) was dissolved in dry MeOH (2 mL), cooled in an ice-salt bath before adding cHCl solution (0.2 mL), and stirring at R.T. for 2 hours. Poured directly onto a 5 g SCX column. Washed with MeOH (2×10 mL), before eluting the compound with NH3 in MeOH 94×10 mL). Solvent evaporated. Residue purified on a 5 g sek-pak column eluting with Pent to EtOAc to 10% MeOH/EtOAc. Solvent evaporated to afford the title compound as a white solid.

Workup

  1. temperaturecooled in an ice-salt bath
  2. additionPoured directly onto a 5 g SCX column
  3. washWashed with MeOH (2×10 mL)
  4. washbefore eluting the compound with NH3 in MeOH 94×10 mL)
  5. customSolvent evaporated
  6. customResidue purified on a 5 g sek-pak column
  7. washeluting with Pent to EtOAc to 10% MeOH/EtOAc
  8. customSolvent evaporated

Sources & evidence

ORD record
ord-75f5b699bf944322885489a0669d5987
Source dataset
uspto-grants-2011_04
Patent number
US07919491B2

Reaction notes

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