Hydrochloric Acid → HCID 23359230, compound

HRID 232857Notes

Reaction equation

HRID 232857 reaction equation
[C:1]([CH2:4][S:5][CH:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][O:9][C:8]2[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][C:27]([Cl:33])=[CH:28][CH:29]=4)[N:24]=3)=[CH:20][C:7]1=2)([OH:3])=O.[C:34]1([S:40]([NH2:43])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl.C(N=C=NCCCN(C)C)C.Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl.O>[C:34]1([S:40]([NH:43][C:1]([CH2:4][S:5][CH:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][O:9][C:8]3[CH:17]=[CH:18][C:19]([O:21][CH2:22][C:23]4[CH:32]=[CH:31][C:30]5[C:25](=[CH:26][C:27]([Cl:33])=[CH:28][CH:29]=5)[N:24]=4)=[CH:20][C:7]2=3)=[O:3])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23359179HCID 23359179, compound

Product 1

HCID 23359230HCID 23359230, compoundYield 28.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.27 g of 11-carboxymethylthio-2-(7-chloroquinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine obtained in Example 21, 0.9 g of benzenesulfonamide and 0.14 g of 4-dimethylaminopyridine and 0.11 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride dissolved in 10 ml of methylene chloride were stirred at room temperature for 7 days. After 10 ml of water and 1.13 ml of 1N-hydrochloric acid were added to the reaction mixture, the organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The residue obtained by removing the solvent was applied to silica gel column chromatography to obtain 0.1 g of the title compound as light brown powder.

Workup

  1. customthe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained
  5. customby removing the solvent

Sources & evidence

ORD record
ord-cb9d186d8229479c8b3f3dea2619fd34
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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