Sodium Hydroxide → 3-(3-{3-[4-(4-Biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-2-imino-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid

HRID 410364ノート

反応式

HRID 410364 の反応式
C([O:3][C:4](=[O:51])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N:31]4[CH2:36][CH2:35][N:34]([CH2:37][C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=5[C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[CH2:33][CH2:32]4)=[CH:27][CH:26]=3)[C:16]2=[NH:50])[CH:6]=1)C.[OH-].[Na+]>CO>[C:39]1([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=1[CH2:37][N:34]1[CH2:33][CH2:32][N:31]([C:28]2[CH:27]=[CH:26][C:25]([CH2:24][N:17]3[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:15]([CH2:14][CH2:13][CH2:12][O:11][C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:4]([OH:51])=[O:3])[C:16]3=[NH:50])=[CH:30][CH:29]=2)[CH2:36][CH2:35]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 585649503-(3-{3-[4-(4-Biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-2-imino-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid ethyl ester

生成物 1

HCID 462411073-(3-{3-[4-(4-Biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-2-imino-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid収率 52%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

To a solution of 3-(3-{3-[4-(4-biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-2-imino-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid ethyl ester (20 mg, 0.03 mmol) in MeOH (2 ml) at rt was added 1M NaOH (2 ml). The reaction was heated at to 80° C. for 5 h and then concentrated under reduced pressure. The material that remained was partitioned between EtOAc and H2O and the organic layer was separated, dried (Na2SO4), filtered and concentrated under reduced pressure to give 3-(3-{3-[4-(4-biphenyl-2-ylmethyl-piperazin-1-yl)-benzyl]-2-imino-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid (10 mg, 52%). HPLC-MS [M+1]+ 327. 1H NMR (500 MHz, CHLOROFORM-d) □ ppm 2.13 (2 H, br s), 2.36 (4 H, br s), 2.87 (4 H, br. s.), 3.39 (2 H, s), 3.99 (2 H, br s), 4.39 (2 H, br s), 5.24-5.55 (2 H, m), 6.37-6.87 (3 H, m), 7.09 (7 H, br s), 7.29-7.67 (11 H, m).

後処理

  1. concentrationconcentrated under reduced pressure
  2. customThe material that remained was partitioned between EtOAc and H2O
  3. customthe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3d1f1da8796c414ca7f83ebcf5380348
出典データセット
uspto-grants-2014_06
特許番号
US08759520B2

反応ノート

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