Water → HCID 66865483, 화합물

HRID 251879노트

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HRID 251879 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][C@H:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20].[N:21]([C:24]([CH3:30])([CH3:29])[C:25](OC)=[O:26])=[C:22]=[O:23].O>ClCCl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][C@H:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[C:25](=[O:26])[C:24]([CH3:30])([CH3:29])[NH:21][C:22]1=[O:23]

참가 물질

5

반응물 3

HCID 962WaterHCID 2769374Methyl 2-isocyanato-2-methylpropanoateHCID 66864574HCID 66864574, 화합물

생성물 1

HCID 66865483HCID 66865483, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(R)-2-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine (50 mg, enantiomer B, preparation as described in WO2004085404) was dissolved in absolute dichloromethane (5 ml), and methyl 2-isocyanato-2-methylpropionate was added dropwise with stirring. After being stirred for 3 h and left to stand overnight, the mixture was admixed with water, the phases were separated and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC. The fractions comprising product were purified, the acetonitrile was removed on a rotary evaporator, and the aqueous residue was neutralized with saturated potassium carbonate solution and extracted three times with ethyl acetate. After the combined ethyl acetate phases had been dried over magnesium sulfate, they were filtered and concentrated to dryness. The residue was dissolved in acetonitrile (1 ml) and admixed with 10% hydrochloric acid. After stirring for 2 h, the mixture was diluted with water (3 ml) and freeze-dried. 68 mg of the title compound were obtained.

후처리

  1. stirringAfter being stirred for 3 h
  2. waitleft
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted twice with dichloromethane
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by means of preparative HPLC
  9. customwere purified
  10. customthe acetonitrile was removed on a rotary evaporator
  11. extractionextracted three times with ethyl acetate
  12. dry with materialAfter the combined ethyl acetate phases had been dried over magnesium sulfate, they
  13. filtrationwere filtered
  14. concentrationconcentrated to dryness
  15. dissolutionThe residue was dissolved in acetonitrile (1 ml)
  16. stirringAfter stirring for 2 h
  17. additionthe mixture was diluted with water (3 ml)
  18. customfreeze-dried

출처 및 근거

ORD 기록
ord-43c105ff516d429d8fe93d090328ec85
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868003B2

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