Sodium Bicarbonate → 1-(3-(1H-benzo[d]imidazol-4-yl)phenoxy)-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

HRID 1399891ノート

反応式

HRID 1399891 の反応式
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH:12]([OH:38])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[C:29]3[N:28]=[CH:27][N:26](COCC[Si](C)(C)C)[C:25]=3[CH:24]=[CH:23][CH:22]=2)[CH:16]=1.C([O-])(O)=O.[Na+]>CCO.Cl>[NH:26]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([C:17]3[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=3)[O:14][CH2:13][CH:12]([OH:38])[CH2:11][N:2]3[CH2:3][CH2:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:1]3)[C:29]=2[N:28]=[CH:27]1

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 867292841-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-4-yl)phenoxy)propan-2-ol

生成物 1

HCID 867292861-(3-(1H-benzo[d]imidazol-4-yl)phenoxy)-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol収率 25%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1-(3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-4-yl)phenoxy)propan-2-ol (265 mg, 0.5 mmol) in EtOH (20 mL) and conc. HCl (1 mL) was stirred at 80° C. overnight. The reaction was adjusted to pH 9 by aq. NaHCO3. The mixture was then extracted with DCM and the combined organic layers dried over Na2SO4 and concentrated to give the crude product. The crude product was purified by pre-HPLC to afford the desired product (50 mg, Yield 25%). 1H NMR (400 MHz, DMSO-d6) δ 8.43 (s, 1H), 8.35 (s, 2H), 7.65 (br.s, 2H), 7.49 (m, 1H), 7.21 (dd, J=7.6 Hz, 1H), 7.12-7.06 (m, 5H), 4.53-4.39 (m, 3H), 4.14 (s, 2H), 2.83-2.57 (m, 6H). LCMS (m/z): 400.1 (M+1).

後処理

  1. extractionThe mixture was then extracted with DCM
  2. dry with materialthe combined organic layers dried over Na2SO4
  3. concentrationconcentrated
  4. customto give the crude product
  5. customThe crude product was purified by pre-HPLC

出典と根拠

ORDレコード
ord-c96c3b16378448c4aeea56747b3ce87d
出典データセット
uspto-grants-2014_12
特許番号
US08906900B2

反応ノート

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