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Hydrochloric Acid → 1-{[1-(Biphenyl-3-ylmethyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentanecarboxylic acid

HRID 2178451
ノート
印刷プレビュー

反応式

HRID 2178451 の反応式
[C:1]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19]4[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]=4)=[CH:16][C:11]=3[N:10]=[C:9]2[CH2:29][C:30]2([C:35]([O:37]C)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:2]=1.C1COCC1.[Li+].[OH-].Cl>C(Cl)Cl.O.CO>[C:1]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH2:18][C:19]4[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]=4)=[CH:16][C:11]=3[N:10]=[C:9]2[CH2:29][C:30]2([C:35]([OH:37])=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:2]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90415001methyl 1-((1-([1,1'-biphenyl]-3-ylmethyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentane-carboxylate

生成物 1

HCID 862826061-{[1-(Biphenyl-3-ylmethyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentanecarboxylic acid

試薬・触媒・溶媒

3
HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

To a 20 mL vial were added methyl 1-((1-([1,1′-biphenyl]-3-ylmethyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentane-carboxylate (51.4 mg, 0.08 mmol), THF (1 mL) and MeOH (1 mL) followed by with LiOH (1 mL, 1 M). The reaction mixture was capped and heated to 80° C. for 3 h. The mixture was cooled to RT, water (5 mL) was added and the pH was adjusted to 4 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 to provide the title compound. MS (ESI): mass calcd. for C37H33N3O3, 567.25; m/z found, 568.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.19 (d, J=8.6, 1H), 8.11 (d, J=8.1, 1H), 7.83 (d, J=8.3, 1H), 7.77-7.71 (m, 1H), 7.69 (d, J=8.6, 1H) 7.58-7.51 (m, 2H), 7.49-7.33 (m, 7H), 7.29 (s, 1H), 7.25-7.22 (m, 1H), 7.11-7.06 (m, 1H), 6.96 (d, J=7.6, 1H), 5.44 (s, 2H), 5.37 (s, 2H), 3.09 (s, 2H), 2.41-2.33 (m, 2H), 1.71-1.63 (m, 2H), 1.47-1.36 (m, 4H).

後処理

  1. customThe reaction mixture was capped
  2. temperatureThe mixture was cooled to RT
  3. customThe organic layer was separated
  4. concentrationthen concentrated to dryness
  5. customThe resulting residue was purified

出典と根拠

ORDレコード
ord-fff7fb8fd5884859bc6b6f09d47c7906
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09067917B2

反応ノート

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