Sodium Hydroxide → HCID 178484233, 화합물

HRID 1922414노트

반응식

HRID 1922414 반응식
[CH3:1][N:2]([CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=[O:32])C(=O)OC1C=CC=CC=1.[OH-].[Na+]>CCO.O>[CH3:1][NH:2][CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=[O:32]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 178484234Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

생성물 1

HCID 178484233HCID 178484233, 화합물

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매2회

실험 절차

Phenyl methyl(2-(2-oxo-6-(thiophene-2-carboximidamido)-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate (700 mg, 1.56 mmol) was stirred in EtOH (20 mL). To this suspension was added solid NaOH (624 mg, 15.6 mmol), followed by water (10 mL). The flask was then fitted with a condenser and was heated to reflux for 2 h. When TLC analysis showed that the reaction was complete, the mixture was cooled to room temperature and diluted with water. The product was extracted with dichloromethane (3×) and the combined organics were dried, filtered and concentrated, then chromatographed in EtOAc, followed by 10% 2M NH3/MeOH in dichloromethane. The isolated spot was then triturated with methanol and ether. Yield (223 mg, 43%). 1H NMR (DMSO-d6) δ 7.73 (d, 1H, J=3.6 Hz), 7.59 (d, 1H, J=5.4 Hz), 7.10 (m, 2H), 6.73 (m, 2H), 6.45 (brs, 2H), 3.91 (t, 1H, J=7.2 Hz), 2.81 (t, 1H, J=7.2 Hz), 2.65 (t, 1H, J=7.2 Hz), 2.50 (t, 1H, J=7.2 Hz); ESI-MS (m/z, %): 329 (MH+, 70), 149 (100), 141 (80), 127 (96).

후처리

  1. customThe flask was then fitted with a condenser
  2. temperaturewas heated
  3. temperatureto reflux for 2 h
  4. extractionThe product was extracted with dichloromethane (3×)
  5. customthe combined organics were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed in EtOAc
  9. customThe isolated spot was then triturated with methanol and ether
  10. customYield (223 mg, 43%)

출처 및 근거

ORD 기록
ord-8eeb00cb81614f3a8408e6d33bb8da0b
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173813B2

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