Trimethylsilyl isocyanate → HCID 23289845, compound

HRID 366788Notes

Reaction equation

HRID 366788 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[CH:6]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:29])[CH2:22][CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[CH2:17][CH2:16]3)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3.[Si]([N:36]=[C:37]=[O:38])(C)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[CH:6]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:29])[CH2:22][CH:23]4[CH2:24][CH2:25][N:26]([C:37]([NH2:36])=[O:38])[CH2:27][CH2:28]4)[CH2:17][CH2:16]3)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 23289901HCID 23289901, compound

Product 1

HCID 23289845HCID 23289845, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(8-Chloro-5,11-dihydro-[1]benzothiepino[4,3-b]pyridin-11-yl)-1-(4-piperidine-acetyl)piperazine (270 mg, 0.591 mmol) was added to anhydrous CH2Cl2 (2.7 ml). TMSNCO (320 mg, 0.37 ml, 2.36 mmol) was added by syringe. The mixture was stirred at room temperature for 90 hours and then quenched with saturated NaHCO3. More water and CH2Cl2 were added, and the mixture was shaken and separated. The aqueous phase was extracted with CH2Cl2 (4×20 ml), and the combined organic phases were washed with brine, dried (Na2SO4), decanted and concentrated. The crude residue was purified by flash chromatography (5%MeOH/CH2Cl2 to 10%MeOH/CH2Cl2 /NH4OH) and the pure product was obtained (295 mg, 66%) MS (FAB, M+H)=529.

Workup

  1. customquenched with saturated NaHCO3
  2. additionMore water and CH2Cl2 were added
  3. stirringthe mixture was shaken
  4. customseparated
  5. extractionThe aqueous phase was extracted with CH2Cl2 (4×20 ml)
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customdecanted
  9. concentrationconcentrated
  10. customThe crude residue was purified by flash chromatography (5%MeOH/CH2Cl2 to 10%MeOH/CH2Cl2 /NH4OH)
  11. customthe pure product was obtained (295 mg, 66%)

Sources & evidence

ORD record
ord-fbfe9ccc1e3a45d7ae20d0fd054dbe36
Source dataset
uspto-grants-2000_10
Patent number
US06130229

Reaction notes

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