Ethyl bromoacetate → HCID 54045489, compound

HRID 1532344Notes

Reaction equation

HRID 1532344 reaction equation
[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH2:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[C:21](=[O:34])[CH:22]([N:24]([CH:31]3[CH2:33][CH2:32]3)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:23])[N:9]2[CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].C([N:38](C(C)C)CC)(C)C.C(OC(=O)CBr)C>C(#N)C>[C:1]([C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH2:14][CH2:15][C@@H:16]3[CH2:20][CH2:19][CH2:18][N:17]3[C:21](=[O:34])[CH:22]([N:24]([CH:31]3[CH2:33][CH2:32]3)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH3:23])[N:9]2[CH2:12][CH3:13])=[CH:5][CH:4]=1)(=[NH:38])[NH2:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 54300405HCID 54300405, compound

Product 1

HCID 54045489HCID 54045489, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

467 mg of ethyl 2-[[2-[(S)-2-[2-(6-cyano-1-ethylindol-2-yl)ethyl]pyrrolidinyl]-1-methyl-2-oxoethyl]cyclopropylamino]acetate was dissolved in 15 ml of acetonitrile, and diisopropylethylamine and ethyl-2-bromoacetate were added thereto. The reaction mixture was heated to 70° C. and stirred for 4 hours. The reaction solution was concentrated under reduced pressure to obtain the residue, which was then purified with silica gel column chromatography [eluent: dichloromethane/methanol (20:1)] to obtain 538 mg of the title compound as a pale yellow oil.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customto obtain the residue, which
  3. customwas then purified with silica gel column chromatography [eluent: dichloromethane/methanol (20:1)]

Sources & evidence

ORD record
ord-cc6f77da71024888b36cfb560aa16504
Source dataset
uspto-grants-2001_03
Patent number
US06201006B1

Reaction notes

Loading…