Diisopropylethylamine → 6-Chloro-pyrimidine-4-carboxylic acid (2-methyl-4-sulfamoyl-phenyl)amide

HRID 1946673Notes

Reaction equation

HRID 1946673 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][C:13]=1[CH3:22].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[CH3:22][C:13]1[CH:14]=[C:15]([S:18](=[O:20])(=[O:19])[NH2:21])[CH:16]=[CH:17][C:12]=1[NH:11][C:8]([C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[CH:6][N:5]=1)=[O:9]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1430374-Amino-3-methylbenzene-1-sulfonamideHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 594470566-Chloro-pyrimidine-4-carboxylic acid (2-methyl-4-sulfamoyl-phenyl)amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A cooled (0° C.) solution of 6-chloropyrimidine-4-carbonyl chloride (4.56 g; 25.8 mmol) in DCM (80 ml) was treated dropwise over 30 minutes with a solution of 4-amino-3-methyl-benzenesulfonamide (4.00 g; 21.5 mmol) and DIEA (7.40 ml; 43.0 mmol) in anhydrous DMF (10 mL). At the end of addition the reaction mixture was concentrated under vacuum and the residue was taken up in EtOAc (200 mL). The organic phase was washed with water/brine (80 mL). A precipitate was formed, which was filtered and dried under vacuum to afford the crude product which was recrystallized from EtOH. The title product was obtained as a white solid.

Workup

  1. additionAt the end of addition the reaction mixture
  2. concentrationwas concentrated under vacuum
  3. washThe organic phase was washed with water/brine (80 mL)
  4. customA precipitate was formed
  5. filtrationwhich was filtered
  6. customdried under vacuum
  7. customto afford the crude product which
  8. customwas recrystallized from EtOH

Sources & evidence

ORD record
ord-5f4cf04e994248afa176b6e8d14f5bd3
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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