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 1714041Notes

Reaction equation

HRID 1714041 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-949d4cf94f3c45dbb2045ddb614f863b
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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