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

HRID 1842144Notes

Reaction equation

HRID 1842144 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-77ff7b29e205473d8c0dc9759094ead2
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

Loading…