1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59621347, compound

HRID 1693225Notes

Reaction equation

HRID 1693225 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 59621240HCID 59621240, compound

Product 1

HCID 59621347HCID 59621347, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-N-[(4aR*,6R*,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) (1.65 g) was dissolved in methanol (60 mL). Then, DBU (1.24 mL, specific gravity: 1.018 g/cm3) was added, and the mixture was stirred with heating under reflux 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 (1.16 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 13 hours and 30 minutes
  3. waitThe reaction solution was left
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by NH-silica gel column chromatography

Sources & evidence

ORD record
ord-21baedf5edf14ec9bd97cf132767de87
Source dataset
uspto-grants-2012_04
Patent number
US08158620B2

Reaction notes

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