Sodium hydride → HCID 178490766, 화합물

HRID 1913133

반응식

HRID 1913133 반응식
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.[H-].[Na+].F[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[CH3:23])[C:19](=[O:24])[N:18]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[CH:17]=[CH:16]2>CC(N(C)C)=O>[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([O:9][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][C:22]=2[CH3:23])[C:19](=[O:24])[N:18]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[CH:17]=[CH:16]3)[CH2:5][CH2:4]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 592260436-fluoro-2-(4-methoxybenzyl)-7-methylisoquinolin-1(2H)-oneHCID 178479278HCID 178479278, 화합물

생성물 1

HCID 178490766HCID 178490766, 화합물

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

반응 조건

온도
80 °C

실험 절차

To a solution of 1.48 g (9.75 mmol) of trans-4-aminocyclohexanol hydrochloride in 20 ml of dimethylacetamide where added 1.95 g (48.77 mmol) of sodium hydride (60%) and the mixture was stirred for 15 minutes. Subsequently 2.90 g (9.75 mmol) of 6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one in 30 ml of dimethylacetamide were added and the reaction mixture was heated to 80° C. for 2 days. After cooling the mixture was poured into 300 ml of ice water and the precipitated crude product was purified by chromatography. First the remaining starting material was eluted with ethyl acetate/heptane (2:1) und finally the desired product was eluted by pure methanol giving 1.98 g 6-(trans-4-amino-cyclohexyloxy)-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one.

후처리

  1. temperatureAfter cooling the mixture
  2. customthe precipitated crude product
  3. customwas purified by chromatography
  4. washwas eluted with ethyl acetate/heptane (2:1) und finally the desired product
  5. washwas eluted by pure methanol giving 1.98 g 6-(trans-4-amino-cyclohexyloxy)-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one

출처 및 근거

ORD 기록
ord-d164da1ab9ac42fa81ce475e2166d472
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609691B2

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