Ethyl Acetate → 4-[6-(2,6-Diethyl-phenyl)-3-(2,2-dimethyl-morpholin-4-ylmethyl)-2-methyl-pyridin-4-yloxy]-2-hydroxy-benzamide

HRID 251640

反応式

HRID 251640 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH2:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:16][CH3:17])[N:5]=[C:4]([CH3:18])[C:3]=1[CH2:19][N:20]1[CH2:25][CH2:24][O:23][C:22]([CH3:27])([CH3:26])[CH2:21]1.[OH:28][C:29]1[CH:37]=[C:36]([OH:38])[CH:35]=[CH:34][C:30]=1[C:31]([NH2:33])=[O:32].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN1CCCC1=O.[Cu].O>[CH2:16]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([CH2:14][CH3:15])[C:8]=1[C:6]1[N:5]=[C:4]([CH3:18])[C:3]([CH2:19][N:20]2[CH2:25][CH2:24][O:23][C:22]([CH3:27])([CH3:26])[CH2:21]2)=[C:2]([O:38][C:36]2[CH:35]=[CH:34][C:30]([C:31]([NH2:33])=[O:32])=[C:29]([OH:28])[CH:37]=2)[CH:7]=1)[CH3:17]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 766012,4-DihydroxybenzamideHCID 596782124-[4-Chloro-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-ylmethyl]-2,2-dimethyl-morpholine

生成物 1

HCID 596782004-[6-(2,6-Diethyl-phenyl)-3-(2,2-dimethyl-morpholin-4-ylmethyl)-2-methyl-pyridin-4-yloxy]-2-hydroxy-benzamide

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
150 °C

実験手順

A mixture of 4-[4-chloro-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-ylmethyl]-2,2-dimethyl-morpholine (30 mg, 0.08 mmol), 2,4-dihydroxy-benzamide (24 mg, 0.16 mmol), copper powder (10 mg) and K2CO3 (22 mg, 0.16 mmol) in 1-methyl-2-pyrrolidinone (1 mL) is heated at 150° C. overnight. After cooling, EtOAc (10 mL) and water (10 mL) are added to the mixture. The organic layer is separated, washed with brine (3×), dried (Na2SO4) and concentrated. The crude is purified by PTLC (1:1 Hexane/EtOAc) to give to give the title compound. 1H NMR (CDCl3) 12.41 (s, 1H), 7.35 (d, 2H), 7.23 (m, 1H), 7.10 (m, 2H), 6.63 (s, 1H), 6.51 (m, 2H), 5.85 (br, 2H), 3.72 (m, 2H), 3.56 (s, 2H), 2.74 (s, 3H), 2.41-2.30 (m, 6H), 1.20 (s, 6H), 1.76 (m, 2H), 1.01 (t, 6H).

後処理

  1. temperatureAfter cooling
  2. customThe organic layer is separated
  3. washwashed with brine (3×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude is purified by PTLC (1:1 Hexane/EtOAc)
  7. customto give

出典と根拠

ORDレコード
ord-ebfd6dff89d84a428eb099852a7ad6e2
出典データセット
uspto-grants-2011_01
特許番号
US07863454B2

関連ノート

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