Dimethylamine, hydrochloride → 3-(2-(4-Dimethylaminomethyl-benzyl)-4-methyl-1-oxo-1,2-dihydro-isoquinolin-6-yl)-4-methyl-benzoic acid, methyl ester

HRID 907324노트

반응식

HRID 907324 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[NH:17][CH:16]=[C:15]2[CH3:23].[H-].[Na+].Cl[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34]Cl)=[CH:30][CH:29]=1.Cl.[CH3:37][NH:38][CH3:39]>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:37][N:38]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][N:17]2[CH:16]=[C:15]([CH3:23])[C:14]3[C:19](=[CH:20][CH:21]=[C:12]([C:3]4[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=4[CH3:1])[C:6]([O:8][CH3:9])=[O:7])[CH:13]=3)[C:18]2=[O:22])=[CH:30][CH:29]=1)[CH3:39]

참가 물질

8

반응물 4

HCID 10473Dimethylamine, hydrochlorideHCID 12171alpha,alpha'-Dichloro-p-xyleneHCID 24758Sodium hydrideHCID 575517644-Methyl-3-(4-methyl-1-oxo-1,2-dihydro-isoquinolin-6-yl)-benzoic acid, methyl ester

생성물 1

HCID 575517203-(2-(4-Dimethylaminomethyl-benzyl)-4-methyl-1-oxo-1,2-dihydro-isoquinolin-6-yl)-4-methyl-benzoic acid, methyl ester

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of the product of Example 93 step ii) in DMF (10 mL) was treated with 60% sodium hydride in mineral oil (0.12 g) and the mixture was stirred at room temperature under a nitrogen atmosphere for 20 mins before the addition of 1,4-di(chloromethyl)benzene (0.74 g). After stirring for a further 20 mins the reaction was treated with dimethylamine hydrochloride (0.98 g), followed by triethylamine (5 mL). Stirring was continued for 16 hours before being diluted with ethyl acetate (150 mL) and washing with water (150 mL). The organic layer was dried with anhydrous sodium sulphate and concentrated in vacuo to give a brown oil, which was purified (SiO2, eluting with ethyl acetate containing 2.5% MeOH and 0.25% triethylamine) to give the sub-titled compound (0.25 g).

후처리

  1. stirringStirring
  2. waitwas continued for 16 hours
  3. washwashing with water (150 mL)
  4. dry with materialThe organic layer was dried with anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customto give a brown oil, which
  7. customwas purified
  8. wash(SiO2, eluting with ethyl acetate containing 2.5% MeOH and 0.25% triethylamine)

출처 및 근거

ORD 기록
ord-74a987fc88af4bc29388dac8012e1f38
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012979B2

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