Triethylamine → HCID 21432722, compound

HRID 2399106Notes

Reaction equation

HRID 2399106 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].C(N(CC)CC)C.[CH2:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[N:22][C:21]([C:27](Cl)=[O:28])=[CH:20]2)[CH3:16]>C(Cl)Cl>[CH2:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[N:23]=[N:22][C:21]([C:27]([NH:6][CH2:5][C:4]([O:3][CH3:2])=[O:7])=[O:28])=[CH:20]2)[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 21432745HCID 21432745, compound

Product 1

HCID 21432722HCID 21432722, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of glycine methyl ester hydrochloride (2.5 g.) and triethylamine (2.6 ml.) in dry methylene chloride (10 ml.) was added to a solution of 6-ethylcinnolin-3-yl carbonyl chloride (1.1 g.) in dry methylene chloride (10 ml.). The resulting solution was kept at room temperature for 5 hours, diluted with methylene chloride (80 ml.) and washed successively with N-hydrochloric acid, water, 10% w/v sodium bicarbonate solution, and water and then dried (MgSO4). The solvent was evaporated and the solid residue was crystallized from aqueous ethanol to give 6-ethyl-N-(methoxycarbonylmethyl)-cinnolin-3-yl carboxamide, m.p. 135°-137° C.

Workup

  1. washwashed successively with N-hydrochloric acid, water, 10%
  2. dry with materialdried (MgSO4)
  3. customThe solvent was evaporated
  4. customthe solid residue was crystallized from aqueous ethanol

Sources & evidence

ORD record
ord-39a2a01a7ce74eb28d5befd88029a2d7
Source dataset
uspto-grants-1977_05
Patent number
US04027023

Reaction notes

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