Thionyl Chloride → 2-[2-(4-Cyanophenyl)ethyl]quinazolin-7-yl-carboxylic acid-n-phenyl-n-(2-methoxycarbonylethyl)amide

HRID 50367Notes

Reaction equation

HRID 50367 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:20]=[CH:19][C:18]3[C:13](=[CH:14][C:15]([C:21](O)=[O:22])=[CH:16][CH:17]=3)[N:12]=2)=[CH:5][CH:4]=1)#[N:2].S(Cl)(Cl)=O.[C:28]1([NH:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(C(C)C)C(C)C)C>>[C:28]1([N:34]([CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])[C:21]([C:15]2[CH:14]=[C:13]3[C:18]([CH:19]=[N:20][C:11]([CH2:10][CH2:9][C:6]4[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=4)=[N:12]3)=[CH:17][CH:16]=2)=[O:22])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 89103N-Phenyl-beta-alanine methyl esterHCID 184124472-[2-(4-Cyanophenyl)-ethyl]-quinazoline-7-carboxylic acid

Product 1

HCID 184125512-[2-(4-Cyanophenyl)ethyl]quinazolin-7-yl-carboxylic acid-n-phenyl-n-(2-methoxycarbonylethyl)amide

Procedure

0.4 g (1.3 mmol) of 2-[2-(4-cyanophenyl)ethyl]quinazoline-7-carboxylic acid and 5 mL of thionyl chloride were stirred for 60 minutes at 50° C. Then the thionyl chloride was distilled off, the residue was dissolved in methylene chloride, mixed with 0.24 g (1.3 mmol) of methyl 3-(N-phenylamino)propionate and 0.22 mL of (1.3 mmol) of N-ethyldiisopropylamine and stirred for 18 hours at ambient temperature. After evaporation of the solvent in vacuo, the residue was chromatographed on silica gel and eluted with methylene chloride containing 1% methanol. Yield: 230 mg (37% of theory); Rf value: 0.64 (silica gel, methylene chloride/methanol=9:1).

Workup

  1. distillationThen the thionyl chloride was distilled off
  2. dissolutionthe residue was dissolved in methylene chloride
  3. customAfter evaporation of the solvent in vacuo
  4. customthe residue was chromatographed on silica gel
  5. washeluted with methylene chloride containing 1% methanol

Sources & evidence

ORD record
ord-1ca0ec59fb844341af24f6eff189b6ef
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

Loading…