7-Chloro-1H-pyrrolo[3,2-b]pyridine → {1-(4-chlorobenzyl)-2-oxo-2-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester

HRID 1192305Notes

Reaction equation

HRID 1192305 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][NH:10][C:3]=12.[C:11]([O:15][C:16](=[O:35])[NH:17][CH:18]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:19](=[O:26])[N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([CH3:14])([CH3:13])[CH3:12]>C1(C)C(C)=CC=CC=1>[C:11]([O:15][C:16](=[O:35])[NH:17][CH:18]([CH2:27][C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:19](=[O:26])[N:20]1[CH2:21][CH2:22][N:23]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[CH:9][NH:10][C:3]=23)[CH2:24][CH2:25]1)([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 224762367-Chloro-1H-pyrrolo[3,2-b]pyridineHCID 67538094[1-(4-Chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 67539194{1-(4-chlorobenzyl)-2-oxo-2-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl esterYield 8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 7-Chloro-1H-pyrrolo[3,2-b]pyridine (40 mg, 0.262 mmol) in xylene (4 mL) and TEA (1 mL) was added [1-(4-chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl ester (0.1 g, 0.27 mol). The mixture was refluxed for 6 days. The solvent was removed under vacuum and the residue was subject to purification by HPLC to afford {1-(4-chlorobenzyl)-2-oxo-2-[4-(1H-pyrrolo[3,2-b]pyridin-7-yl)-piperazin-1-yl]-ethyl}-carbamic acid tert-butyl ester (10 mg, 8%). 1H NMR (CDCl3, 400 Hz) δ 11.81 (s, 1H), 7.95 (d, J=6.4 Hz, 1H), 7.40 (s, 1H), 7.15 (d, J=8.00 Hz, 2H), 6.46 (d, J=6.8 Hz, 2H), 5.42 (d, J=8.4 Hz, 1H), 4.82 (d, J=7.2 Hz, 1H), 3.87-3.28 (m, 8H), 2.98 (d, J=6.4 Hz, 2H), 1.41 (s, 9H). MS (ESI+) [M+H]+ 484.

Workup

  1. temperatureThe mixture was refluxed for 6 days
  2. customThe solvent was removed under vacuum
  3. customthe residue was subject to purification by HPLC

Sources & evidence

ORD record
ord-687856ef97f44c5ab506e4ce89fa00cc
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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