Diisopropylethylamine → 2-Phenyl-pyrimidine-5-carboxylic acid (2-sulfamoyl-ethyl)-amide

HRID 219684Notes

Reaction equation

HRID 219684 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13](Cl)=[O:14])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:16][CH2:17][CH2:18][S:19]([NH2:22])(=[O:21])=[O:20].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[S:19]([CH2:18][CH2:17][NH:16][C:13]([C:10]1[CH:9]=[N:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:12][CH:11]=1)=[O:14])(=[O:21])(=[O:20])[NH2:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 101263TaurinamideHCID 106326372-phenylpyrimidine-5-carbonyl Chloride

Product 1

HCID 166661752-Phenyl-pyrimidine-5-carboxylic acid (2-sulfamoyl-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenyl-pyrimidine-5-carboxylic acid chloride (1.51 mmol) and 2-amino-ethanesulfonic acid amide (1.51 mmol) in DCM (15 mL) is added diisopropylethylamine (4.53 mmol). The mixture is stirred at room temperature overnight. The mixture is concentrated in vacuo. The residue is washed with water and DCM to afford 2-phenyl-pyrimidine-5-carboxylic acid (2-sulfamoyl-ethyl)-amide as a solid. MS: 307 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 3.25 (q, 2H), 3.67 (m, 2H), 6.93 (s, N—H), 7.47-7.60 (m, 3H), 8.36-8.48 (m, 2H), 8.92-9.15 (m, N—H), 9.16-9.36 (m, 2H); IC50=55 nM.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. washThe residue is washed with water and DCM

Sources & evidence

ORD record
ord-369611d106f543dc8e23599b32b3dc2b
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

Loading…