1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57827291, compound

HRID 1693214Notes

Reaction equation

HRID 1693214 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]12[CH2:17][C@@H:16]([O:18][CH3:19])[CH2:15][CH2:14][C@H:13]1[CH2:12][S:11][C:10]([NH:20]C(=O)C1C=CC=CC=1)=[N:9]2.C1CCN2C(=NCCC2)CC1>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]12[CH2:17][C@@H:16]([O:18][CH3:19])[CH2:15][CH2:14][C@H:13]1[CH2:12][S:11][C:10]([NH2:20])=[N:9]2

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57827164HCID 57827164, compound

Product 1

HCID 57827291HCID 57827291, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-N-[(4aR*,7S*,8aS*)-8a-(2-Fluorophenyl)-7-methoxy-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-yl]benzamide obtained in Preparation Example 57-(7) (268 mg) was dissolved in methanol (8 mL). Then, DBU (202 μL, specific gravity: 1.018 g/cm3) was added, and the mixture was stirred with heating under reflux for four hours and 15 minutes. Then, the reaction solution was stirred at 64° C. for 13 hours and 30 minutes. Thereafter, the reaction solution was stirred with heating under reflux for nine hours and 30 minutes. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure. The residue was purified by NH-silica gel column chromatography to obtain the title compound (150 mg).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for four hours and 15 minutes
  3. stirringThen, the reaction solution was stirred at 64° C. for 13 hours and 30 minutes
  4. stirringThereafter, the reaction solution was stirred
  5. temperaturewith heating
  6. temperatureunder reflux for nine hours and 30 minutes
  7. waitThe reaction solution was left
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-bc8afc579a714461af72e5583fbcb78d
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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