Triethylamine → N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N2,N2-bis(4-methoxybenzyl)-5,6-dimethyl-3-nitropyridin-2,4-diamine

HRID 606089ノート

反応式

HRID 606089 の反応式
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:14]=2)[C:5]([CH3:25])=[C:4]([CH3:26])[N:3]=1.C(N(CC)CC)C.[CH3:34][O:35][C:36]1[CH:52]=[CH:51][C:39]([CH2:40][NH:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=2)=[CH:38][CH:37]=1>C1(C)C=CC=CC=1>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:14]=[C:13]([CH2:12][NH:11][C:6]3[C:5]([CH3:25])=[C:4]([CH3:26])[N:3]=[C:2]([N:41]([CH2:40][C:39]4[CH:38]=[CH:37][C:36]([O:35][CH3:34])=[CH:52][CH:51]=4)[CH2:42][C:43]4[CH:44]=[CH:45][C:46]([O:49][CH3:50])=[CH:47][CH:48]=4)[C:7]=3[N+:8]([O-:10])=[O:9])[O:17][N:16]=2)=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 714952Bis(4-methoxybenzyl)amineHCID 866168882-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-5,6-dimethyl-3-nitropyridin-4-amine

生成物 1

HCID 69450751N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N2,N2-bis(4-methoxybenzyl)-5,6-dimethyl-3-nitropyridin-2,4-diamine収率 94%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Under a nitrogen atmosphere, 2-chloro-N-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-5,6-dimethyl-3-nitropyridin-4-amine (25.00 g, 66.35 mmol), toluene (250 mL), triethylamine (11.1 mL, 79.6 mmol), and N,N-bis(4-methoxybenzyl)amine (18.8 g, 73.0 mmol) were combined and heated at reflux for three days. The volatiles were removed under reduced pressure, and the residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate. The ethyl acetate layer was separated and concentrated under reduced pressure. The residue was dissolved in dichloromethane, and the resulting solution was washed sequentially with water and brine. The combined aqueous fractions were extracted with ethyl acetate. The combined organic fractions were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude solid was triturated with ethanol, isolated by filtration, and washed with diethyl ether to provide 37.29 g of N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-N2,N2-bis(4-methoxybenzyl)-5,6-dimethyl-3-nitropyridin-2,4-diamine as an orange solid.

後処理

  1. temperatureheated
  2. temperatureat reflux for three days
  3. customThe volatiles were removed under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and saturated aqueous potassium carbonate
  5. customThe ethyl acetate layer was separated
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in dichloromethane
  8. washthe resulting solution was washed sequentially with water and brine
  9. extractionThe combined aqueous fractions were extracted with ethyl acetate
  10. dry with materialThe combined organic fractions were dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customThe crude solid was triturated with ethanol
  14. customisolated by filtration
  15. washwashed with diethyl ether

出典と根拠

ORDレコード
ord-b81bc1f050e4493c97a057ede4be5ac1
出典データセット
uspto-grants-2011_03
特許番号
US07915281B2

反応ノート

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