Triethylamine → HCID 53748710, compound

HRID 1900545Notes

Reaction equation

HRID 1900545 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[O:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[C:9]([N:11]3[CH2:19][C@H:18]4[N:14]([CH2:15][CH:16]([O:20]C(C)(C)C)[CH2:17]4)[CH2:13][CH2:12]3)=[N:10][C:4]=2[CH:3]=1.C(N(CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[O:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[C:9]([N:11]3[CH2:19][C@H:18]4[N:14]([CH2:15][CH:16]([OH:20])[CH2:17]4)[CH2:13][CH2:12]3)=[N:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 57005561HCID 57005561, compound

Product 1

HCID 53748710HCID 53748710, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

8-chloro-11-[(6S)-8-t-butoxy-1,4-diazabicyclo[4.3.0]non-4-yl]-dibenzo[b,f]-1,4-oxazepine (0.211 g, 0.495 mmol), prepared as described above, was dissolved in trifluoroacetic acid (10 mL) and stirred for 15 minutes. The solvent was removed and the resulting residue was redissolved in methylene chloride (20 mL). Triethylamine (0.100 g, 0.991 mmol) was then added via syringe and the resulting solution was stirred for 1 hour. Washing with water (50 mL), drying over MgSO4 and concentrating resulted in a white solid (0.180 g, 99%); mp 94°-96° C.; Rf(35% acetone/hexanes): 0.15; HRMS (FAB) MH+ of C20H20N3O2Cl, calculated 370.1322, found 370.1 318.

Workup

  1. customThe solvent was removed
  2. dissolutionthe resulting residue was redissolved in methylene chloride (20 mL)
  3. stirringthe resulting solution was stirred for 1 hour
  4. washWashing with water (50 mL)
  5. dry with materialdrying over MgSO4
  6. concentrationconcentrating

Sources & evidence

ORD record
ord-b7f64c82c8cb4691af7106b97c00d513
Source dataset
uspto-grants-1996_11
Patent number
US05576314

Reaction notes

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