1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59621266, compound

HRID 1842136Notes

Reaction equation

HRID 1842136 reaction equation
[CH2:1]([O:8][C@H:9]1[CH2:27][C@:13]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[N:14]=[C:15]([NH:18]C(=O)C3C=CC=CC=3)[S:16][CH2:17][C@@H:12]2[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1>CO>[CH2:1]([O:8][C@H:9]1[CH2:27][C@:13]2([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[N:14]=[C:15]([NH2:18])[S:16][CH2:17][C@@H:12]2[CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 67477922HCID 67477922, compound

Product 1

HCID 59621266HCID 59621266, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-N-[(4aR*,7R*,8aS*)-7-Benzyloxy-8a-(2-fluorophenyl)-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-yl]benzamide obtained in Preparation Example 58-(6) (1.81 g) was dissolved in methanol (60 mL). Then, DBU (1.14 mL, specific gravity: 1.018 g/cm3) was added, and the mixture was stirred with heating under reflux for three hours. Then, the reaction solution was stirred at 64° C. for 14 hours. 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 (1.20 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for three hours
  3. stirringThen, the reaction solution was stirred at 64° C. for 14 hours
  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-6f792bec3caa4f3f9ec58b480f2b69af
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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