2-Chlorodibenz(b,f)-1,4-oxazepin-11(10H)-one → HCID 70283170, compound

HRID 1941142Notes

Reaction equation

HRID 1941142 reaction equation
N(Cl)Cl.[Cl:4][C:5]1[CH:20]=[CH:19][C:8]2[S:9][C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=O)[NH:13][C:7]=2[CH:6]=1.ClC1C=CC2OC3C=CC=CC=3C(=O)NC=2C=1.[C:38]([O:42][C@@H:43]1[CH2:51][N:50]2[C@H:45]([CH2:46][NH:47][CH2:48][CH2:49]2)[CH2:44]1)([CH3:41])([CH3:40])[CH3:39]>C(#N)C>[Cl:4][C:5]1[CH:20]=[CH:19][C:8]2[S:9][C:10]3[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=3[C:12]([N:47]3[CH2:46][C@H:45]4[N:50]([CH2:51][C@@H:43]([O:42][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:44]4)[CH2:49][CH2:48]3)=[N:13][C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 766192-Chlorodibenz(b,f)-1,4-oxazepin-11(10H)-oneHCID 76939Chlorimide2×HCID 8271058-chlorodibenzo[b,f][1,4]thiazepin-11(10H)-oneHCID 54556930HCID 54556930, compound

Product 1

HCID 70283170HCID 70283170, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The iminochloride of 8-chloro-10,11-dihydrodibenz[b,f]-1,4-thiazepine-11-one (0.580 g, 2.07 mmol), prepared in a like manner to the iminochloride of 8-chloro-10,11-dihydrodibenz[b,f]-1,4-oxazepine-11-one described in example 2(a), was dissolved in anhydrous acetonitrile (20 mL) under argon and (6S,8S)-8-t-butoxy-1,4-diazabicyclo[4.3.0]nonane (0.970 g, 4.89 mmol) was added as a solution in anhydrous acetonitrile (5 mL) via syringe and the resulting solution was heated to reflux for 5 hours. After cooling to room temperature, the solvent was evaporated under reduced pressure and the residue partitioned between water and methylene chloride. The organic layer was washed with brine, dried (MgSO4) and evaporated to dryness. The product was purified on silica gel using 10% acetone in hexanes as the eluent to give 0.34 g (37%) of 8-chloro-11-[(6S,8S)-8-t-butoxy-1,4-diazabicyclo[4.3.0]non-4-yl]-dibenz[b,f]-1,4-thiazepine as an off-white solid; mp 132°-134° C.; Rf (10% acetone/hexanes): 0.10; HRMS (FAB): MH+ of C24H28 N3OSCl, calculated 442.1720, found 442.1728.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 5 hours
  3. customthe solvent was evaporated under reduced pressure
  4. customthe residue partitioned between water and methylene chloride
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customThe product was purified on silica gel using 10% acetone in hexanes as the eluent

Sources & evidence

ORD record
ord-73e18eca4eb142939a9beeee86906d30
Source dataset
uspto-grants-1997_12
Patent number
US05703072

Reaction notes

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