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Water → [3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenyl]-carbamic Acid 2-dimethylamino-ethyl Ester-Hydrochloride Salt

HRID 1072527
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HRID 1072527 반응식
Cl.[N+](C1C=C[C:8]([O:11][C:12](=[O:33])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]3[C:29]4[C:24](=[C:25]([Cl:31])[CH:26]=[C:27]([Cl:30])[CH:28]=4)[CH2:23][N:22]([CH3:32])[CH2:21]3)[CH:15]=2)=[CH:7]C=1)([O-])=O.[CH3:34][N:35](C)[CH2:36]CO.O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[ClH:30].[CH3:34][N:35]([CH3:36])[CH2:7][CH2:8][O:11][C:12](=[O:33])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]2[C:29]3[C:24](=[C:25]([Cl:31])[CH:26]=[C:27]([Cl:30])[CH:28]=3)[CH2:23][N:22]([CH3:32])[CH2:21]2)[CH:15]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 79022-(Dimethylamino)ethanolHCID 11430Potassium CarbonateHCID 223868924-Nitrophenyl [3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]carbamate hydrochloride2회

생성물 1

HCID 69802468[3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenyl]-carbamic Acid 2-dimethylamino-ethyl Ester-Hydrochloride Salt
수율 73.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

Under stirring and argon atmosphere [3(6,8-dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenyl]-carbamic acid 4-nitro-phenyl ester—hydrochloride salt (15 mg, example 151, intermediate 1) was suspended in dichloromethane (1.5 ml) and 2-dimethylamino-ethanol (3 mg) dissolved in dichloromethane (0.5 ml) was added. After stirring for 6 h and standing over night dichloromethane, water and saturated potassium carbonate solution were added. The organic layer was separated, washed three times with saturated potassium carbonate solution, dried over magnesium sulphate, filtered and concentrated in vacuo. The crude material was purified by preparative HPLC. The product containing fractions were combined and the acetonitrile was removed in vaccuo. After addition of sodium bicarbonate the aqueous phase was extracted with ethyl acetate. The organic layer was separated, dried (magnesium sulphate), filtered and concentrated in vaccuo. The residue was dissolved in water/2N hydrochloric acid and freeze dried to give 5 mg of the title compound.

후처리

  1. additionwas added
  2. stirringAfter stirring for 6 h
  3. waitstanding over night
  4. customThe organic layer was separated
  5. washwashed three times with saturated potassium carbonate solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by preparative HPLC
  10. additionThe product containing fractions
  11. customthe acetonitrile was removed in vaccuo
  12. additionAfter addition of sodium bicarbonate the aqueous phase
  13. extractionwas extracted with ethyl acetate
  14. customThe organic layer was separated
  15. dry with materialdried (magnesium sulphate)
  16. filtrationfiltered
  17. concentrationconcentrated in vaccuo
  18. dissolutionThe residue was dissolved in water/2N hydrochloric acid
  19. customfreeze dried

출처 및 근거

ORD 기록
ord-c40e2415e62c4f788c7b8a7f5b759091
출처 데이터셋
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06911453B2

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