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

HRID 1714072ノート

反応式

HRID 1714072 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-61e15052f39c40d781f8037a3bf89027
出典データセット
uspto-grants-2010_09
特許番号
US07795247B2

反応ノート

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