Acetic Acid → 1'-({6-Chloro-1-[(1-methylpyrrolidin-3-yl)methyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4'-piperidine]

HRID 1866024Notes

Reaction equation

HRID 1866024 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:17]([N:19]3[CH2:24][CH2:23][C:22]4([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=5[CH2:26][O:25]4)[CH2:21][CH2:20]3)=[O:18])=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:16][CH2:15][NH:14][CH2:13]2)=[CH:4][CH:3]=1.[CH3:33]C(O)=O.[BH3-]C#N.[Na+]>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:17]([N:19]3[CH2:24][CH2:23][C:22]4([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=5[CH2:26][O:25]4)[CH2:21][CH2:20]3)=[O:18])=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:16][CH2:15][N:14]([CH3:33])[CH2:13]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 59657701HCID 59657701, compound

Product 1

HCID 596575131'-({6-Chloro-1-[(1-methylpyrrolidin-3-yl)methyl]-1H-indol-3-yl}carbonyl)-3H-spiro[2-benzofuran-1,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1′-{[6-chloro-1-(pyrrolidin-3-ylmethyl)-1H-indol-3-yl]carbonyl}-3H-spiro[2-benzofuran-1,4′-piperidine] in MeOH was treated with aq. H2CO (1.5 eq), AcOH (1.1 eq) and stirred for 15 min at room temperature, then treated with NaCNBH3 (1.1 eq) and stirred at room temperature for 1 h. Concentration and purification by preparative HPLC gave the desired product. ES-MS m/e (%): 464.2 (M+H+).

Workup

  1. stirringstirred at room temperature for 1 h
  2. concentrationConcentration and purification by preparative HPLC

Sources & evidence

ORD record
ord-6b228fa44a484f92b8c13f5010c86c8d
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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