HCID 66640061, compound → HCID 66640764, compound

HRID 37944Notes

Reaction equation

HRID 37944 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:18])[CH:15]=2)[C:10]([C:26]([C:29]#[N:30])(C)C)=[CH:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:19]([N:17]([CH3:18])[C:14]1[CH:15]=[C:16]2[C:11]([C:10]([CH2:26][C:29]#[N:30])=[CH:9][NH:8]2)=[CH:12][CH:13]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 66640061HCID 66640061, compound

Product 1

HCID 66640764HCID 66640764, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 6-(benzyl-methyl-amino)-3-(cyano-dimethyl-methyl)-indole-1-carboxylic acid tert-butyl ester (26.4 g, 90%, 58.9 mmol) in DCM-TFA (2:1, 180 mL) was stirred for 20 h at 20° C. Evaporation of solvent gave a crude, which was redissolved in DCM and the solution was washed with water, aqueous sodium bicarbonate and water and dried over MgSO4. Evaporation of solvent gave a solid, which was triturated with hexane to give [6-(benzyl-methyl-amino)-1H-indol-3-yl]-acetonitrile as a solid (14.3 g). MS (ES): 304 (MH+). [6-(benzyl-methyl-amino)-1H-indol-3-yl]-acetonitrile was then treated in a manner similar to that described in Step 34D-H, but using greater than three equivalents of iodomethane, to give 6-(benzyl(methyl)amino)-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester.

Workup

  1. customEvaporation of solvent
  2. customgave a crude, which
  3. washthe solution was washed with water, aqueous sodium bicarbonate and water
  4. dry with materialdried over MgSO4
  5. customEvaporation of solvent
  6. customgave a solid, which
  7. customwas triturated with hexane

Sources & evidence

ORD record
ord-3376733973064c89bd19bb001decd1a7
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

Loading…