Acetic Acid → methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)-3-thienyl]-1H-indole-6-carboxylate

HRID 1714041ノート

反応式

HRID 1714041 の反応式
[C:1]([O:5][C:6](=[O:34])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[C:10]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[C:9]1[C:27]1[CH:31]=[CH:30][S:29][C:28]=1[CH:32]=O)([CH3:4])([CH3:3])[CH3:2].[CH3:35][N:36]([CH3:40])[CH2:37][CH2:38][NH2:39].CC(O)=O.[BH3-]C#N.[Na+]>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6](=[O:34])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=2)[C:10]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[C:9]1[C:27]1[CH:31]=[CH:30][S:29][C:28]=1[CH2:32][NH:39][CH2:38][CH2:37][N:36]([CH3:40])[CH3:35])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 86604968methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(2-formyl-3-thienyl)-1H-indole-6-carboxylate

生成物 1

HCID 68511147methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)-3-thienyl]-1H-indole-6-carboxylate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-(2-formyl-3-thienyl)-1H-indole-6-carboxylate in THF (0.05 M) was treated with N,N-dimethylethane-1,2-diamine (10 eq) and the pH was adjusted to 6 with AcOH; after stirring for 1 h at RT solvent was removed and the residue dissolved in MeOH (0.05M), then NaCNBH3 (1.5 eq) was added and the mixture was stirred during the weekend. The reaction mixture was diluted with EtOAc and washed with water and brine, dried over Na2SO4 and evaporated affording methyl 1-(2-tert-butoxy-2-oxoethyl)-3-cyclohexyl-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)-3-thienyl]-1H-indole-6-carboxylate.

後処理

  1. customwas removed
  2. dissolutionthe residue dissolved in MeOH (0.05M)
  3. stirringthe mixture was stirred during the weekend
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

出典と根拠

ORDレコード
ord-949d4cf94f3c45dbb2045ddb614f863b
出典データセット
uspto-grants-2010_09
特許番号
US07795247B2

反応ノート

読み込み中…