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

HRID 1051517노트

반응식

HRID 1051517 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6921af4b1a8a48c8935d59b00bac8151
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388173B2

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