Trimethylsilyl isocyanate → HCID 9827175, compound

HRID 366789Notes

Reaction equation

HRID 366789 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6](=[C: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.O>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6](=[C: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

5

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 9933648HCID 9933648, compound

Product 1

HCID 9827175HCID 9827175, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by a similar procedure from 4-[2-[4-(8-chloro-5,11-dihydro-[1]benzothiepino[4,3-b]pyridin-11-ylidene)-1-piperidinyl]-2-oxoethyl]-piperidine (120 mg, 0.265 mmol) in CH2Cl2 (3 ml), to which TMSNCO (200 μl, 170 mmol) was added at 0° C. After 5 minutes at 0° C., the mixture was stirred 3.5 hours at room temperature. The reaction mixture was diluted with water and extracted with CH2Cl2 ; the organic phase was washed with NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated. The product was chromatographed on silica in 5%MeOH/CH2Cl2 and eluted with 10%MeOH/CH2Cl2 to afford a white solid (103 mg); HRMS: calc.: 497.1778; found: 497.1766.

Workup

  1. additionwas added at 0° C
  2. extractionextracted with CH2Cl2
  3. washthe organic phase was washed with NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was chromatographed on silica in 5%MeOH/CH2Cl2
  8. washeluted with 10%MeOH/CH2Cl2

Sources & evidence

ORD record
ord-d1bc8c4eb5104c5098a4921ba3f9ede2
Source dataset
uspto-grants-2000_10
Patent number
US06130229

Reaction notes

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