Triethylamine → N-[2-[bis(4-methoxybenzyl)amino]-4-({[3-(4-fluorophenyl)isoxazol-5-yl]methyl}amino)-5,6-dimethylpyridin-3-yl]-2-ethoxyacetamide

HRID 606093Notes

Reaction equation

HRID 606093 reaction equation
[CH2:1]([O:3][CH2:4][C:5](Cl)=[O:6])[CH3:2].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH2:20][NH:21][C:22]3[C:27]([CH3:28])=[C:26]([CH3:29])[N:25]=[C:24]([N:30]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=4)[CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)[C:23]=3[NH2:49])[O:17][N:16]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[CH3:48][O:47][C:44]1[CH:43]=[CH:42][C:41]([CH2:40][N:30]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)[C:24]2[C:23]([NH:49][C:5](=[O:6])[CH2:4][O:3][CH2:1][CH3:2])=[C:22]([NH:21][CH2:20][C:18]3[O:17][N:16]=[C:15]([C:12]4[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=4)[CH:19]=3)[C:27]([CH3:28])=[C:26]([CH3:29])[N:25]=2)=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84189Ethoxyacetyl chloride2×HCID 69453189N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N2,N2-bis(4-methoxybenzyl)-5,6-dimethylpyridine-2,3,4-triamine

Product 1

HCID 67041304N-[2-[bis(4-methoxybenzyl)amino]-4-({[3-(4-fluorophenyl)isoxazol-5-yl]methyl}amino)-5,6-dimethylpyridin-3-yl]-2-ethoxyacetamideYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, ethoxyacetyl chloride (1.4 g, 11 mmol) was added dropwise to a solution of N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N2,N2-bis(4-methoxybenzyl)-5,6-dimethylpyridine-2,3,4-triamine (5.898 g, 10.39 mmol) and triethylamine (2.2 mL, 15 mmol) in dichloromethane (30 mL) at 0° C. After the reaction was stirred for 0.7 hours, an analysis by HPLC indicated the presence of starting material, and additional ethoxyacetyl chloride (0.54 g) was added. The stirring was continued, and after 1.5 hours, the reaction mixture was diluted with dichloromethane and washed sequentially with saturated aqueous potassium carbonate, water, and brine; dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 6.2 g of N-[2-[bis(4-methoxybenzyl)amino]-4-({[3-(4-fluorophenyl)isoxazol-5-yl]methyl}amino)-5,6-dimethylpyridin-3-yl]-2-ethoxyacetamide as a yellow oil.

Workup

  1. additionwas added
  2. waitafter 1.5 hours
  3. washwashed sequentially with saturated aqueous potassium carbonate, water, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3136aa501f31486499527504df6739a1
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

Loading…