Trifluoroacetic acid → HCID 11261756, compound

HRID 1295635Notes

Reaction equation

HRID 1295635 reaction equation
C1(OC)C=CC=CC=1.C(OC([N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH2:25][C@@H:26]2[CH2:31][N:30]3[CH2:32][C:33]([C:36]4[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=4)=[CH:34][CH2:35][C@@H:29]3[CH2:28][N:27]2[C:42](=[O:57])[C:43]2[CH:48]=[C:47]([C:49]([F:52])([F:51])[F:50])[CH:46]=[C:45]([C:53]([F:56])([F:55])[F:54])[CH:44]=2)=[CH:17]1)=O)(C)(C)C.C(OC(N1C2C(=CC=CC=2)C(C[C@@H]2CN3C=C(C4C=CN=CC=4)CC[C@@H]3CN2C(=O)C2C=C(C(F)(F)F)C=C(C(F)(F)F)C=2)=C1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:56][C:53]([F:54])([F:55])[C:45]1[CH:44]=[C:43]([C:42]([N:27]2[C@H:26]([CH2:25][C:18]3[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[NH:16][CH:17]=3)[CH2:31][N:30]3[CH:32]=[C:33]([C:36]4[CH:37]=[CH:38][N:39]=[CH:40][CH:41]=4)[CH2:34][CH2:35][C@@H:29]3[CH2:28]2)=[O:57])[CH:48]=[C:47]([C:49]([F:50])([F:51])[F:52])[CH:46]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 58910082HCID 58910082, compoundHCID 58910086HCID 58910086, compound

Product 1

HCID 11261756HCID 11261756, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To mixture of anisole (35 mg), (3R,9aR)-3-[2-(3,5-bis(trifluoromethyl)-benzoyl)-7-pyridin-4-yl-1,3,4,6,9,9a-hexahydro-2H-pyrido[1,2-a]pyrazin-3-ylmethyl]-indole-1-carboxylic acid tert-butyl ester and (3R,9aR)-3-[2-(3,5-bis(trifluoromethyl)-benzoyl)-7-pyridin-4-yl-1,3,4,8,9,9a-hexahydro-2H-pyrido[1,2-a]pyrazin-3-ylmethyl]-indole-1-carboxylic acid tert-butyl ester (0.20 g) in dichloromethane (2 ml) was added trifluoroacetic acid, at 0° C. After 1.5 h at room temperature the mixture was diluted with dichloromethane, quenched with ice, and carefully basified with ammonium hydroxide. The layers were separated, the organic layer dried filtered and concentrated in vacuo. The residue was dissolved in methanol and heated at 50° C. for 1 h, then cooled to room temperature and concentrated in vacuo. The residual solid was stirred with hexanes overnight and then collected by filtration to afford (3R,9aR)-(3,5-bis(trifluoromethyl)phenyl)-[3-(1H-indol-3-ylmethyl)-7-pyridin-4-yl-1,3,4,8,9,9a-hexahydro-pyrido[1,2-a]pyrazin-2-yl]-methanone (compound 1) (70 mg). Rf 0.51 (SiO2, CH2Cl2/MeOH/NH4OH 93:7:0.5).

Workup

  1. customat 0° C
  2. customquenched with ice
  3. customThe layers were separated
  4. customthe organic layer dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in methanol
  8. temperaturecooled to room temperature
  9. concentrationconcentrated in vacuo
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6b7f43f85bf5484d8e6bef5d69f3b20d
Source dataset
uspto-grants-2007_07
Patent number
US07244734B2

Reaction notes

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