Diisopropylethylamine → HCID 57920211, compound

HRID 216044Notes

Reaction equation

HRID 216044 reaction equation
[CH3:1][C:2]1([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17](=[O:20])(=[O:19])[NH2:18])[CH:12]=2)=[O:9])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl[C:22]1[C:23]2[C:30]([CH3:31])=[CH:29][NH:28][C:24]=2[N:25]=[CH:26][N:27]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[CH3:1][C:2]1([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17](=[O:20])(=[O:19])[NH2:18])[CH:12]=2)=[O:9])[CH2:3][CH2:4][N:5]([C:22]2[C:23]3[C:30]([CH3:31])=[CH:29][NH:28][C:24]=3[N:25]=[CH:26][N:27]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 63121615HCID 63121615, compound

Product 1

HCID 57920211HCID 57920211, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
105 °C

Procedure

4-Methyl-N-(3-sulfamoylphenyl)piperidine-4-carboxamide from step B (33 mg, 0.098 mmol), 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (16 mg, 0.098 mmol), N,N-diisopropylethylamine (51 mg, 0.39 mmol), and isopropanol (1.0 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 preparative HPLC to give the title compound in 21% yield.

Workup

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

Sources & evidence

ORD record
ord-aab474b9d4f24e5fb4a6b85874bb70c7
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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