Chlorotrimethylsilane → HCID 136337167, compound

HRID 1428838Notes

Reaction equation

HRID 1428838 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][C:9](=[N:20]C(OCC)=O)[N:10]2[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[N:11]2)=[O:7])=[CH:4][C:3]=1[N:28]1[CH2:37][CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29]1.Cl[Si](C)(C)C>ClCCCl>[Cl:1][C:2]1[CH:27]=[C:26]2[C:5]([C:6](=[O:7])[NH:8][C:9]([N:10]3[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[N:11]3)=[N:20]2)=[CH:4][C:3]=1[N:28]1[CH2:37][CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 86644123HCID 86644123, compound

Product 1

HCID 136337167HCID 136337167, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1-{[4-chloro-3-(3,4-dihydro-1H-isoquinolin-2-yl)-benzoylamino]-ethoxycarbonylimino-methyl}-1H-pyrazole-4-carboxylic acid, ethyl ester (1.2 g, 2.4 mmol), DCE (5 mL) and chlorotrimethylsilane (2.8 mL, 22 mmol) was heated to 110° C. for 16 h in a sealed tube. The vessel was cooled in an ice bath for 1 h, and the resulting precipitate was collected by filtration, washed with cold DCE, and dried under vacuum to provide the titled compound (0.40 g, 19%). MS (ESI): mass calcd. for C23H20ClN5O3, 449.9; m/z found, 450.1 [M+H]+.

Workup

  1. temperatureThe vessel was cooled in an ice bath for 1 h
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with cold DCE
  4. customdried under vacuum

Sources & evidence

ORD record
ord-76d81899db5c4c4d97f562813f5d48df
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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