Hydrochloric Acid → HCID 11495505, compound

HRID 2233761Notes

Reaction equation

HRID 2233761 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[C:5]([CH3:17])[N:6]2[CH2:11][C:12]([O:14]CC)=[O:13].C(N(CC)CC)C.[CH2:33]([S:35](Cl)(=[O:37])=[O:36])[CH3:34].Cl>CC#N.CO.[OH-].[Na+].O>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][C:4]2[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[NH:1][S:35]([CH2:33][CH3:34])(=[O:37])=[O:36])[N:6]([CH2:11][C:12]([OH:14])=[O:13])[C:5]=2[CH3:17])=[CH:24][CH:23]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 86609239HCID 86609239, compound

Product 1

HCID 11495505HCID 11495505, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

The product from step (iv) (250 mg) was dissolved in CH3CN (10 ml). Triethylamine (300 μl) added, followed by ethanesulphonyl chloride (170 μl) and the mixture stirred for 20 h. The reaction was then diluted with MeOH (5 ml), 1M sodium hydroxide (2.1 ml) added and stirred for 5 h. The mixture was diluted with water, acidified with 2M hydrochloric acid, extracted with EtOAc, dried (MgSO4) and evaporated. The residue was purified using reverse phase preparative chromatography (eluent MeCN/NH3(aq)) to give the title compound. Yield 190 mg.

Workup

  1. additionadded
  2. stirringstirred for 5 h
  3. extractionextracted with EtOAc
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-1d19a8982fdc43569ecca4dbf2ee049c
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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