1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59621327, compound

HRID 1693224Notes

Reaction equation

HRID 1693224 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@:8]12[CH2:17][CH2:16][C@H:15]([O:18][CH3:19])[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][CH2:16][C@H:15]([O:18][CH3:19])[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 59621295HCID 59621295, compound

Product 1

HCID 59621327HCID 59621327, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-N-[(4aR*,6S*,8aS*)-8a-(2-Fluorophenyl)-6-methoxy-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-yl]benzamide obtained in Preparation Example 59-(8) (3.11 g) was dissolved in methanol (100 mL). Then, DBU (2.34 mL, specific gravity: 1.018 g/cm3) was added, and the mixture was stirred with heating under reflux for two hours and 15 minutes. Then, the reaction solution was stirred at 64° C. for 13 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 (1.96 g).

Workup

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

Sources & evidence

ORD record
ord-c738ea2115744144922b639b58d12868
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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