Trimethylsilyl isocyanate → HCID 18617655, compound

HRID 1264315Notes

Reaction equation

HRID 1264315 reaction equation
[NH2:1][CH2:2][C:3]([C:6]1[CH:27]=[CH:26][C:9]([C:10]([NH:12][CH2:13][CH2:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH:19]=[C:18]3[C:24]#[N:25])=[O:11])=[CH:8][CH:7]=1)([CH3:5])[CH3:4].C[Si]([N:32]=[C:33]=[O:34])(C)C>O1CCOCC1>[C:24]([C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]([CH2:14][CH2:13][NH:12][C:10](=[O:11])[C:9]3[CH:8]=[CH:7][C:6]([C:3]([CH3:5])([CH3:4])[CH2:2][NH:1][C:33]([NH2:32])=[O:34])=[CH:27][CH:26]=3)[CH:16]=2)[NH:20][CH:19]=1)#[N:25]

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 18617788HCID 18617788, compound

Product 1

HCID 18617655HCID 18617655, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-[2-amino-1,1-dimethyl-ethyl]-N-[2-(3-cyano-1H-indol-5-yl)-ethyl]-benzamide (90 mg, 0.25 mmol) (reference example 105) in 1,4-dioxane (1 ml) was added trimethylsilyl isocyanate (68 μL, 0.50 mmol). The resulting mixture is stirred for 16 h. The precipitated solids are collected by vacuum filtration, washed with a small volume of CH2Cl2 and dried under high vacuum to give 99 mg of product. MS (ion spray) m/z 404 (M+H)+.

Workup

  1. filtrationThe precipitated solids are collected by vacuum filtration
  2. washwashed with a small volume of CH2Cl2
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-11f9d5463e3743e89a58c9592b24c78f
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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