HCID 68508825, compound → HCID 68508758, compound

HRID 1714030Notes

Reaction equation

HRID 1714030 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:27][C:28](OC)=[O:29])[C:10]3[C:15]([C:16]=2[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:14][CH:13]=[C:12]([C:23]([O:25][CH3:26])=[O:24])[CH:11]=3)=[C:4]([CH2:32][NH:33][CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[CH:3]=1.CO[Na]>CO.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3=[C:16]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[C:15]4[CH:14]=[CH:13][C:12]([C:23]([O:25][CH3:26])=[O:24])=[CH:11][C:10]=4[N:9]3[CH2:27][C:28](=[O:29])[N:33]([CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[CH2:32][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 68508825HCID 68508825, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 68508758HCID 68508758, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-[4-chloro-2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl-3-cyclohexyl-1-(2-methoxy-2-oxoethyl)-1H-indole-6-carboxylate (from Step 5) in dry MeOH (0.05 M), 10% in weight of MeONa was added and the mixture stirred at RT overnight. The volume of the solution was reduced in vacuo before being diluted with EtOAc. The organic phase was washed with HCl 1 N, brine. The organic phase was dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound. The crude was then used in the next step without any further purification (quant); MS (ES+) m/z 508 (M+H)+.

Workup

  1. washThe organic phase was washed with HCl 1 N, brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-581c03bd98ce402b9265ee214c1ac7c4
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

Loading…