Triethylamine → HCID 178498257, compound

HRID 380415Notes

Reaction equation

HRID 380415 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1>ClCCl>[CH3:14][O:13][C:10]1[C:11]2[N:12]=[C:22]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[NH:1][C:2]=2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 183583-(Chloromethyl)pyridineHCID 22663264Benzoic acid, 2,3-diamino-4-methoxy-, methyl ester (9CI)

Product 1

HCID 178498257HCID 178498257, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2,3-diamino-4-methoxybenzoate [0.73 g, Reference Example 8(a)] and triethylamine (0.94 g) in dry dichloromethane (20 ml), at 0° C., was treated with nicotinyl chloride (0.53 g). The reaction mixture was stirred at ambient temperature for 2 hours and then evaporated. The residue was dissolved in acetic acid (8 ml) and the solution heated at 80° C. for 2 hours. After cooling to room temperature the reaction mixture was treated with water. The insoluble material was subjected to flash chromatography on silica to give the title compound (0.46 g). NMR (CDCl3): δ 4.00(s,3H), 4.15(s,3H), 6.70(d,1H), 7.40(m,1H), 7.90(d,1H), 8.45(m,1H), 8.75(d,1H), 9.30(d,1H), 10.80(s,1H)].

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in acetic acid (8 ml)
  3. temperaturethe solution heated at 80° C. for 2 hours
  4. temperatureAfter cooling to room temperature the reaction mixture
  5. additionwas treated with water

Sources & evidence

ORD record
ord-f855a703372941bba53a5c88c29cf655
Source dataset
uspto-grants-2001_10
Patent number
US06303600B1

Reaction notes

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