Isopropanol → N-(3-(1H-tetrazol-5-yl)phenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 216047Notes

Reaction equation

HRID 216047 reaction equation
[NH:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH:12][C:13]([C:15]3([CH3:21])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)=[O:14])[CH:9]=[CH:10][CH:11]=2)=[N:4][N:3]=[N:2]1.Cl[C:23]1[C:24]2[C:31]([CH3:32])=[CH:30][NH:29][C:25]=2[N:26]=[CH:27][N:28]=1.C(N(CC)C(C)C)(C)C.C(O)(C)C>CS(C)=O>[NH:4]1[C:5]([C:6]2[CH:7]=[C:8]([NH:12][C:13]([C:15]3([CH3:21])[CH2:20][CH2:19][N:18]([C:23]4[C:24]5[C:31]([CH3:32])=[CH:30][NH:29][C:25]=5[N:26]=[CH:27][N:28]=4)[CH2:17][CH2:16]3)=[O:14])[CH:9]=[CH:10][CH:11]=2)=[N:1][N:2]=[N:3]1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 178431740HCID 178431740, compound

Product 1

HCID 178430821N-(3-(1H-tetrazol-5-yl)phenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamideYield 4.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
105 °C

Procedure

N-(3-(1H-tetrazol-5-yl)phenyl)-4-methylpiperidine-4-carboxamide from step B (93 mg, 0.29 mmol), 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (49 mg, 0.29 mmol), N,N-diisopropylethylamine (0.19 g. 1.45 mmol), isopropanol (4.0 mL), and DMSO (0.5 mL) were combined in a pressure rated sealed tube and heated at 105° C. for 18 hours. The mixture was concentrated, and the residue was purified by preprative HPLC to give the title compound in 4.3% yield.

Workup

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

Sources & evidence

ORD record
ord-7a4525fcaad74211989a71c4ee2dc492
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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