Morpholine → HCID 86598345, compound

HRID 1270422Notes

Reaction equation

HRID 1270422 reaction equation
[CH2:1]([C@@H:8]1[CH2:13][N:12]2[CH2:14][C@@H:15](OS(C)(=O)=O)[CH2:16][CH2:17][C@@H:11]2[CH2:10][N:9]1[C:23](=[O:38])[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1>C(#N)C>[F:31][C:30]([F:33])([F:32])[C:28]1[CH:29]=[C:24]([C:23]([N:9]2[C@H:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][N:12]3[CH2:14][C@H:15]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[CH2:16][CH2:17][C@@H:11]3[CH2:10]2)=[O:38])[CH:25]=[C:26]([C:34]([F:36])([F:35])[F:37])[CH:27]=1.[F:31][C:30]([F:33])([F:32])[C:28]1[CH:29]=[C:24]([C:23]([N:9]2[C@H:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][N:12]3[CH2:14][C@@H:15]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)[CH2:16][CH2:17][C@@H:11]3[CH2:10]2)=[O:38])[CH:25]=[C:26]([C:34]([F:36])([F:35])[F:37])[CH:27]=1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86598344HCID 86598344, compound

Product 2

HCID 86598345HCID 86598345, compoundHCID 86598346HCID 86598346, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methanesulfonic acid (3R,7S,9aR)-3-benzyl-2-(3,5-bis(trifluoromethyl)benzoyl)-octahydropyrido[1,2-a]pyrazin-7-yl ester (1.97 g) and morpholine (0.44 mL) in acetonitrile (50 mL) was heated at 80° C. for 40 hours. After cooling to room temperature the mixture was concentrated in vacuo and the residue purified by flash-chromatography (SiO2, CH2Cl2/MeOH/NH4OH 980:18.75:1.25) to afford 3,5-bis(trifluoromethyl)phenyl-[(3R,7R,9aR)-3-benzyl-7-morpholin-4-yl-octahydropyrido[1,2-a]pyrazin-2-yl]-methanone (0.97 g, Rf 0.24 (CH2Cl2/MeOH/NH4OH 96:3.75:0.25)) (compound 29) and 3,5-bis(trifluoromethyl)phenyl-[(3R,7S,9aR)-3-benzyl-7-morpholin-4-yl-octahydropyrido[1,2-a]pyrazin-2-yl]-methanone (0.75 g, Rf 0.15 (CH2Cl2/MeOH/NH4OH 96:3.75:0.25)) (compound 30).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. concentrationwas concentrated in vacuo
  3. customthe residue purified by flash-chromatography (SiO2, CH2Cl2/MeOH/NH4OH 980:18.75:1.25)

Sources & evidence

ORD record
ord-3b0f3d75cf8b4d4097b5fd11854eb83f
Source dataset
uspto-grants-2007_04
Patent number
US07202238B2

Reaction notes

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