Triethylamine → HCID 21254744, compound

HRID 2287604Notes

Reaction equation

HRID 2287604 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][CH2:13][C:14]([N:16]([C:18]2[C:19]([Cl:39])=[C:20]([C:35]([Cl:38])=[CH:36][CH:37]=2)[CH2:21][O:22][C:23]2[C:31]3[N:30]=[C:29]([O:32][CH3:33])[N:28]([CH3:34])[C:27]=3[CH:26]=[CH:25][CH:24]=2)[CH3:17])=[O:15])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[CH3:48][C:49]1[C:54]([C:55](Cl)=[O:56])=[CH:53][CH:52]=[CH:51][N:50]=1>ClCCl>[Cl:39][C:19]1[C:18]([N:16]([CH3:17])[C:14](=[O:15])[CH2:13][NH:12][C:10](=[O:11])/[CH:9]=[CH:8]/[C:5]2[CH:6]=[N:7][C:2]([NH:1][C:55]([C:54]3[C:49]([CH3:48])=[N:50][CH:51]=[CH:52][CH:53]=3)=[O:56])=[CH:3][CH:4]=2)=[CH:37][CH:36]=[C:35]([Cl:38])[C:20]=1[CH2:21][O:22][C:23]1[C:31]2[N:30]=[C:29]([O:32][CH3:33])[N:28]([CH3:34])[C:27]=2[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 183219202-Methylpyridine-3-carbonyl chloride--hydrogen chloride (1/1)HCID 21254648HCID 21254648, compound

Product 1

HCID 21254744HCID 21254744, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-[N-[(E)-3-(6-aminopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methoxy-1-methyl-1H-benzimidazole (100 mg) and triethylamine (53.3 mg) in dichloromethane (2 ml) was added 2-methyl-3-pyridinecarbonyl chloride hydrochloride (74.2 mg) under ice-cooling, and the mixture was stirred for 15 minutes at the same temperature and then for 3 hours at ambient temperature. The reaction mixture was concentrated, and the residue was dissolved in methanol (3 ml). To the solution was added 1N sodium hydroxide solution (0.5 ml), and the mixture was stirred for 1 hour. Chloroform was added to the reaction mixture, and the solution was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol, 10:1, v/v) to give 4-[2,6-dichloro-3-[N-methyl-N-[(E)-3-[6-(2-methylpyridin-3-carboxamido)pyridin-3-yl]acryloylglycyl]amino]benzyloxy]-2-methoxy-1-methyl-1H-benzimidazole (99 mg).

Workup

  1. temperaturecooling
  2. waitfor 3 hours at ambient temperature
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in methanol (3 ml)
  5. additionTo the solution was added 1N sodium hydroxide solution (0.5 ml)
  6. stirringthe mixture was stirred for 1 hour
  7. additionChloroform was added to the reaction mixture
  8. washthe solution was washed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated in vacuo
  11. customThe residue was purified by preparative thin layer chromatography (chloroform

Sources & evidence

ORD record
ord-324dd1129d3948c287c8b982004dc6cd
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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