Diisopropylethylamine → 3-(4-amino-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamate

HRID 216092Notes

Reaction equation

HRID 216092 reaction equation
[CH3:1][N:2]([CH3:22])[C:3](=[O:21])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([NH2:20])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:13])[CH:6]=1.Cl[C:24]1[C:25]2[C:32]([CH3:33])=[CH:31][NH:30][C:26]=2[N:27]=[CH:28][N:29]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[CH3:1][N:2]([CH3:22])[C:3](=[O:21])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([NH2:20])[CH2:19][CH2:18][N:17]([C:24]3[C:25]4[C:32]([CH3:33])=[CH:31][NH:30][C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:16][CH2:15]2)=[O:13])[CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 670367823-(4-Aminopiperidine-4-carboxamido)phenyl dimethylcarbamate

Product 1

HCID 579202093-(4-amino-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamateYield 55%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

3-(4-aminopiperidine-4-carboxamido)phenyl dimethylcarbamate from step B (0.109 g, 0.36 mmol), 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (0.060 g, 0.36 mmol), and N,N-diisopropylethylamine (0.277 g, 2.14 mmol) were combined in isopropanol (5 mL) and heated in a sealed tube at 120° C. for 18 hours. The mixture was concentrated, and the residue was purification by silica gel chromatography (0-10% MeOH/CH2Cl2) to afford the title compound (0.085 g, 55%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurification by silica gel chromatography (0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2a6eef61a9e74d48b46b5907ca94fdd6
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

Loading…