Triethylamine → HCID 70282518, compound

HRID 1941143Notes

Reaction equation

HRID 1941143 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]2[S: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][C@@H: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[S: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][C@@H: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 70283170HCID 70283170, compound

Product 1

HCID 70282518HCID 70282518, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

8-chloro-11-[(6S,8S)-8-t-butoxy-1,4-diazabicyclo[4.3.0]non-4-yl]-dibenz[b,f]-1,4-thiazepine (0.311 g, 0.704 mmol) was dissolved in trifluoroacetic acid (20 mL) and stirred for 1 hour. The trifluoroacetic acid was removed under reduced pressure and the residue dissolved in methylene chloride (20 mL). Triethylamine (0.142 g, 1.40 mmol) was then added via syringe and the reaction stirred for 1 hour, washed with water, dried (MgSO4) and evaporated to dryness to give 8-chloro-11-[(6S,8S)-8-hydroxy-1,4-diazabicyclo[4.3.0]non-4-yl]-dibenz[b,f]-1,4-thiazepine as an off-white solid (0.197 g, 72%); mp 58°-60° C.; Rf (40% acetone/hexanes): 0.15; HRMS (FAB): MH+ of C20H20N3OSCl, calculated 386.1094, found 386.1085.

Workup

  1. customThe trifluoroacetic acid was removed under reduced pressure
  2. dissolutionthe residue dissolved in methylene chloride (20 mL)
  3. stirringthe reaction stirred for 1 hour
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-31ee516264f340f581b650d4f990d028
Source dataset
uspto-grants-1997_12
Patent number
US05703072

Reaction notes

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