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

HRID 216050Notes

Reaction equation

HRID 216050 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([CH3:20])[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>[CH3:22][N:2]([CH3:1])[C:3](=[O:21])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH3:20])[CH2:15][CH2:16][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)[CH2:18][CH2:19]2)=[O:13])[CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 670367863-(4-Methylpiperidine-4-carboxamido)phenyl dimethylcarbamate

Product 1

HCID 579201983-(4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)phenyl dimethylcarbamateYield 53%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

3-(4-methylpiperidine-4-carboxamido)phenyl dimethylcarbamate from step B (47 mg, 0. 14 mmol) 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (23 mg, 0.138 mmol), N,N-diisopropylethylamine (54 mg, 0.41 mmol), and isopropanol (1.0 mL) were combined in a pressure rated sealed tube and heated at 100° C. for 18 hours. The mixture was concentrated, and the residue was purified by preparative HPLC to give the title compound in 53% yield.

Workup

  1. customrated sealed tube
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b7042ae37264444f81e81d45a5b1ffb1
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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