Lithium Hydroxide → 1-{[1-(4-Furan-3-ylbenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentanecarboxylic acid

HRID 1776756노트

반응식

HRID 1776756 반응식
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:44]=[CH:43][C:9]([CH2:10][N:11]3[C:15]4[CH:16]=[CH:17][C:18]([O:20][CH2:21][C:22]5[CH:31]=[CH:30][C:29]6[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=6)[N:23]=5)=[CH:19][C:14]=4[N:13]=[C:12]3[CH2:32][C:33]3([C:38]([O:40]CC)=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:8][CH:7]=2)=[CH:2]1.C1COCC1.[Li+].[OH-]>CO>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][N:11]3[C:15]4[CH:16]=[CH:17][C:18]([O:20][CH2:21][C:22]5[CH:31]=[CH:30][C:29]6[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=6)[N:23]=5)=[CH:19][C:14]=4[N:13]=[C:12]3[CH2:32][C:33]3([C:38]([OH:40])=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:43][CH:44]=2)=[CH:2]1

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90416780Ethyl 1-((1-(4-(furan-3-yl)benzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate

생성물 1

HCID 862809891-{[1-(4-Furan-3-ylbenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentanecarboxylic acid

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
80 °C

실험 절차

To a 20 mL vial were added ethyl 1-((1-(4-(furan-3-yl)benzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate (60 mg, 0.1 mmol), THF (1.3 mL) and MeOH (1.3 mL) followed by LiOH (1.4 mL, 1 M). The reaction mixture was heated at 80° C. for 1.5 h. The mixture was cooled to RT and concentrated to dryness. Water (5 mL) was added and the pH was adjusted to ˜5-6 using 1 M HCl. To the mixture was added DCM (5 mL) and the mixture was stirred for 1 h at RT. The organic layer was separated then concentrated to dryness. The resulting residue was purified using FCC or reverse phase HPLC to provide the title compound. MS (ESI): mass calcd. for C35H31N3O4, 557.23; m/z found, 558.2 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.22 (d, J=8.5, 1H), 8.10 (d, J=8.5, 1H), 7.84 (d, J=8.1, 1H), 7.77-7.69 (m, 3H), 7.58-7.54 (m, 1H), 7.48-7.46 (m, 1H), 7.42 (d, J=8.1, 2H), 7.35-7.34 (m, 1H), 7.16 (d, J=8.8, 1H), 7.04-7.01 (m, 3H), 6.65 (s, 1H), 5.42 (s, 2H), 5.35 (s, 2H), 3.12 (s, 2H), 2.32-2.26 (m, 2H), 1.73-1.68 (m, 2H), 1.65-1.52 (m, 4H).

후처리

  1. temperatureThe mixture was cooled to RT
  2. concentrationconcentrated to dryness
  3. additionWater (5 mL) was added
  4. additionTo the mixture was added DCM (5 mL)
  5. customThe organic layer was separated
  6. concentrationthen concentrated to dryness
  7. customThe resulting residue was purified

출처 및 근거

ORD 기록
ord-50a64820573445dabc630ed9c1de990a
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265770B2

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