1-Cyclopentylpiperazine → HCID 68567959, compound

HRID 898146Notes

Reaction equation

HRID 898146 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:15][C:9]2=[N:10][C:11](Br)=[CH:12][CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2].[CH:16]1([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:20][CH2:19][CH2:18][CH2:17]1>>[CH2:1]([O:3][C:4]([C:6]1[NH:15][C:9]2=[N:10][C:11]([N:24]3[CH2:25][CH2:26][N:21]([CH:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)[CH2:22][CH2:23]3)=[CH:12][CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 8064211-CyclopentylpiperazineHCID 46839969Ethyl 6-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 68567959HCID 68567959, compoundYield 39.5%

Conditions

Temperature
140 °C

Procedure

A mixture of 1 g (3.7 mmol) 6-bromo-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester (prepared according to the method described in WO 2003/064423 A1) and 2.8 g (18.6 mmol) 1-cyclopentyl-piperazine (commercially available) was heated to 140° C. for 1 h. The mixture was absorbed on isolute and purified by flash column chromatography on silica eluting with a gradient formed from n-heptane and ethyl acetate (0.1% NEt3). Evaporation of the product fractions yielded 501 mg (39%) of the title compound as white solid. MS: (m/e): 343.4 (MH+).

Workup

  1. customprepared
  2. customThe mixture was absorbed on isolute and
  3. custompurified by flash column chromatography on silica eluting with a gradient
  4. customformed from n-heptane and ethyl acetate (0.1% NEt3)
  5. customEvaporation of the product fractions

Sources & evidence

ORD record
ord-7a7dd2e535344f369d5a7928787fdb92
Source dataset
uspto-grants-2008_04
Patent number
US07351708B2

Reaction notes

Loading…