Acetic Acid → methyl 3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl]-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

HRID 1714072노트

반응식

HRID 1714072 반응식
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH:32]=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH2:38].CC(O)=O.[BH3-]C#N.[Na+]>C1COCC1.CCOC(C)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:8]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][NH:38][CH2:37][CH2:36][N:35]([CH3:39])[CH3:34])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 86604971methyl 3-cyclohexyl-2-(2-formylphenyl)-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

생성물 1

HCID 68508941methyl 3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl]-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of methyl 3-cyclohexyl-2-(2-formylphenyl)-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate in THF (0.1 M), N,N-dimethylethane-1,2-diamine (10 eq) was added and the pH adjusted to pH=6 with HOAc. The solution was stirred at RT for 1 h, before the THF was concentrated in vacuo and the residue taken up in MeOH. To the methanolic solution (0.1 M) NaBH3CN (2 eq) was added and the mixture stirred at RT overnight. The reaction mixture was diluted with EtOAc. The organic phase was washed with NaHCO3 (s.s.), H2O and brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The title compound was used as crude in the next step; MS (ES+) m/z 520 (M+H)+.

후처리

  1. concentrationwas concentrated in vacuo
  2. washThe organic phase was washed with NaHCO3 (s.s.), H2O and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-61e15052f39c40d781f8037a3bf89027
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795247B2

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