Morpholine → HCID 86598336, compound

HRID 1270414Notes

Reaction equation

HRID 1270414 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]([N:15]2[C@H:20]([CH2:21][C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:19][N:18]3[C@@H:31]([CH2:34]Cl)[CH2:32][CH2:33][C@@H:17]3[CH2:16]2)=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]([N:15]2[C@H:20]([CH2:21][C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:19][N:18]3[C@@H:31]([CH2:34][N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)[CH2:32][CH2:33][C@@H:17]3[CH2:16]2)=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86598335HCID 86598335, compound

Product 1

HCID 86598336HCID 86598336, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (3,5-bis(trifluoromethyl)phenyl)-[(3R,6R,8aR)-6-chloromethyl-3-(1H-indol-3-ylmethyl)-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-methanone (1.06 g) in dimethylformamide (15 mL) was added morpholine (5 mL). The resulting mixture was heated at 120° C. for 6 hours. After cooling to room temperature, ethyl acetate and 5% aqueous sodiumbicarbonate were added and the layers were separated. The organic layer was dried and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, MTBE/MeOH/NH4OH 95:4.5:0.5) to afford 3,5-bis(trifluoromethyl)phenyl-[(3R,6R,8aR)-3-(1H-indol-3-ylmethyl)-6-(morpholin-4-ylmethyl)-hexahydropyrrolo[1,2-a]pyrazin-2-yl]-methanone (407 mg). Rf 0.46 (MTBE/MeOH/NH4OH 95:4.5:0.5) (compound 2).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe layers were separated
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (SiO2, MTBE/MeOH/NH4OH 95:4.5:0.5)

Sources & evidence

ORD record
ord-099083b2a9bf4308b89197e780898ac7
Source dataset
uspto-grants-2007_04
Patent number
US07202238B2

Reaction notes

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