Hydrochloric Acid → HCID 58009505, compound

HRID 1009492Notes

Reaction equation

HRID 1009492 reaction equation
[Cl:1][C:2]1[C:3]([CH3:33])=[C:4]([N:8]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([OH:19])=O)=[O:11])[CH:5]=[CH:6][CH:7]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:46][S:47]([NH2:50])(=[O:49])=[O:48].C1CCN2C(=NCCC2)CC1.Cl>CN(C=O)C>[Cl:1][C:2]1[C:3]([CH3:33])=[C:4]([N:8]([S:23]([C:26]2[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=2)(=[O:24])=[O:25])[CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH:50][S:47]([CH3:46])(=[O:49])=[O:48])=[O:19])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 24883169HCID 24883169, compound

Product 1

HCID 58009505HCID 58009505, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

182 mg of 3-[({N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycyl}amino)methyl]benzoic acid was dissolved in 0.50 mL of DMF, and 75 mg of 1,1′-carbonyldiimidazole was added thereto, followed by stirring at room temperature for 1 hour. To the reaction liquid were added 40 mg of methane sulfonamide and 66 mg of DBU, followed by stirring at 50° C. for 8 hours. The reaction liquid was acidified by addition of 2.50 mL of 1 M hydrochloric acid, and then extracted with a mixed solvent of chloroform/methanol (5/1), and the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 95:5) to obtain 207 mg of 3-[({N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycyl}amino)methyl]-N-(methylsulfonyl)benzamide.

Workup

  1. customTo the reaction liquid
  2. stirringby stirring at 50° C. for 8 hours
  3. customThe reaction liquid
  4. extractionextracted with a mixed solvent of chloroform/methanol (5/1)
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 95:5)

Sources & evidence

ORD record
ord-8d9cb644bb5741b0b34f1a38d243e939
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

Loading…