Methylamine → (Z)-4-(2-(1-methyl-1H-benzo[d]imidazol-5-yl)-1-(4-(2-(methyl-amino)ethoxy)phenyl)but-1-enyl)phenol

HRID 626245ノート

反応式

HRID 626245 の反応式
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[C:12](\[C:15]2[CH:24]=[CH:23][C:18]3[N:19]([CH3:22])[CH:20]=[N:21][C:17]=3[CH:16]=2)/[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:32][NH2:33]>CO>[CH3:22][N:19]1[C:18]2[CH:23]=[CH:24][C:15](/[C:12](/[CH2:13][CH3:14])=[C:11](/[C:25]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=3)\[C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:33][CH3:32])=[CH:6][CH:7]=3)=[CH:16][C:17]=2[N:21]=[CH:20]1

参加物

4

反応物 2

HCID 6329MethylamineHCID 89672895(Z)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(1-methyl-1H-benzo[d]-imidazol-5-yl)but-1-enyl)phenol

生成物 1

HCID 71615974(Z)-4-(2-(1-methyl-1H-benzo[d]imidazol-5-yl)-1-(4-(2-(methyl-amino)ethoxy)phenyl)but-1-enyl)phenol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
85 °C

実験手順

To a stirred solution of (Z)-4-(1-(4-(2-chloroethoxy)phenyl)-2-(1-methyl-1H-benzo[d]imidazol-5-yl)but-1-enyl)phenol (20 mg, 1.0 eq) in 10 mL MeOH was added 5 mL CH3NH2 (aq) and heated at 85° C. for 72 h. The organic solvent was removed in vacuo, water was added to the residue, and extracted with EtOAc. The extract was dried, concentrated, and purified by column chromatography to give the desired (Z)-product. 1H NMR (400 MHz, CDCl3) δ 7.80 (s, 1H), 7.60 (s, 1H), 7.13 (d, J=8.4 Hz, 1H), 7.08 (d, J=8.4 Hz, 2H), 7.01 (d, J=9.2 Hz, 1H), 6.80 (d, J=8.4 Hz, 2H), 6.75 (d, J=8.8 Hz, 2H), 6.45 (d, J=8.4 Hz, 2H), 3.89 (t, J=5.2 Hz, 2H), 3.80 (s, 3H), 2.88 (t, J=5.2 Hz, 2H), 2.52 (q, J=7.2 Hz, 2H), 2.46 (s, 3H), 0.88 (t, J=7.2 Hz, 3H); m/z=428[M+1]+.

後処理

  1. customThe organic solvent was removed in vacuo, water
  2. additionwas added to the residue
  3. extractionextracted with EtOAc
  4. customThe extract was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography
  7. customto give the desired (Z)-product

出典と根拠

ORDレコード
ord-b4b25ad66ad44290ab096fffb6546c33
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

反応ノート

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