Sodium hydride → 3-Amino-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-3,4-dihydroquinolin-2(1H)-one

HRID 1247522

반응식

HRID 1247522 반응식
[H-].[Na+].Cl.[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:15].CS(O[CH2:21][CH:22]1[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]1)(=O)=O>CN(C=O)C>[NH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH2:21][CH:22]2[CH2:26][O:25][C:24]([CH3:28])([CH3:27])[O:23]2)[C:6]1=[O:15]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 134994283-Amino-3,4-dihydroquinolin-2(1H)-one--hydrogen chloride (1/1)HCID 15570840(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate

생성물 1

HCID 219068213-Amino-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-3,4-dihydroquinolin-2(1H)-one수율 53%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Sodium hydride (60% in oil, 191 mg, 4.70 mmol) was added to 3-amino-3,4-dihydroquinolin-2(1H)-one hydrochloride (J. Med. Chem., 28, 1985; 1511–16,450 mg, 2.27 mmol), in anhydrous DMF (6 mL) at 0° C. over a period of 5 min keeping the internal temperature at <10° C. The reaction was stirred for a further 30 min before addition of (2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate (J. Med. Chem. 35, 1992, 1650–62; 528 mg, 2.50 mmol) and the reaction has then heated to 80° C. for a period of 5 h. The reaction was then cooled and evaporated before addition of sat. aqueous NaHCO3 (20 mL) and EtOAc (50 mL). The organic layer was then dried (MgSO4), filtered and evaporated and the residue was purified by column chromatography (MeOH:DCM 1:19) to afford the title compound (330 mg, 53%) as colourless oil.

후처리

  1. customat <10° C
  2. temperatureThe reaction was then cooled
  3. customevaporated before addition of sat. aqueous NaHCO3 (20 mL) and EtOAc (50 mL)
  4. dry with materialThe organic layer was then dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by column chromatography (MeOH:DCM 1:19)

출처 및 근거

ORD 기록
ord-c9898cd3b4694b7ca5f894223eb35679
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129249B2

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