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 410364노트

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HRID 410364 반응식
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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3d1f1da8796c414ca7f83ebcf5380348
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759520B2

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