1-Chloroethyl chloroformate → HCID 22028200, compound

HRID 731568Notes

Reaction equation

HRID 731568 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH2:21][N:22](C)[CH3:23])[CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.ClC(OC(Cl)C)=O>ClCCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][CH2:21][NH:22][CH3:23])[CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 10067306HCID 10067306, compound

Product 1

HCID 22028200HCID 22028200, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A stirred solution under nitrogen of N-(2-{3-[(3-chlorophenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-1-yl}ethyl)-N,N-dimethylamine (0.540 g, 1.49 mmol) in 1,2-dichloroethane is treated with 1-chloroethyl chloroformate (0.40 mL, 3.7 mmol), heated at reflux temperature for 2 h cooled, and concentrated in vacuo. The resultant residue is treated with ethanol, heated at reflux temperature for 2 h and concentrated in vacuo. This resultant residue is chromatographed using 2:98 concentrated NH4OH:ethanol as eluent to afford the free amine of the title product as a semi-solid (311 mg, 60%). The free amine is dissolved in ethanol, treated with 4M HCl in dioxane and filtered. The filtercake is dried to give the title product as a pale yellow solid, 274 mg (48% yield), mp 263-265° C. (dec.), identified by mass spectral and HNMR analyses.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 2 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. additionThe resultant residue is treated with ethanol
  6. temperatureheated
  7. temperatureat reflux temperature for 2 h
  8. concentrationconcentrated in vacuo
  9. customThis resultant residue is chromatographed

Sources & evidence

ORD record
ord-81654db8b40f4db3b9032896a53608b5
Source dataset
uspto-grants-2009_09
Patent number
US07585873B2

Reaction notes

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