Hydrochloric Acid → HCID 72303226, compound

HRID 1747097Notes

Reaction equation

HRID 1747097 reaction equation
C([O:9][CH2:10][C:11]1[CH:12]=[N+:13]([O-:52])[C:14]([CH2:17][O:18][NH:19][C:20]([CH:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25](=[O:32])[N:24]([CH:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]3[NH:39][S:40]([CH3:43])(=[O:42])=[O:41])[CH:23]2[C:44]2[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][C:45]=2[Cl:51])=[O:21])=[CH:15][CH:16]=1)(=O)C1C=CC=CC=1.[OH-].[Na+].Cl.C(=O)([O-])O.[Na+]>C(O)C.C(Cl)(Cl)Cl>[Cl:51][C:45]1[CH:46]=[C:47]([Cl:50])[CH:48]=[CH:49][C:44]=1[CH:23]1[CH:22]([C:20]([NH:19][O:18][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([CH2:10][OH:9])=[CH:12][N+:13]=2[O-:52])=[O:21])[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](=[O:32])[N:24]1[CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[NH:39][S:40]([CH3:43])(=[O:41])=[O:42]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 72303244HCID 72303244, compound

Product 1

HCID 72303226HCID 72303226, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 153 mg of (6-{[({[(3RS,4RS)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl]carbonyl}amino)oxy]methyl}-1-oxidopyridin-3-yl)methyl benzoate in 3 ml of ethanol was cooled to 0° C., and 32 mg of sodium hydroxide was added thereto, followed by stirring at 0° C. for 2 hours. The solution was neutralized with 1 M hydrochloric acid, and a saturated aqueous sodium hydrogen carbonate solution and chloroform were added for liquid separation. The organic layer was dried over anhydrous magnesium sulfate and then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:chloroform-methanol) to obtain 24 mg of (3RS,4RS)-3-(2,4-dichlorophenyl)-N-{[5-(hydroxymethyl)-1-oxidopyridin-2-yl]methoxy}-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide.

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. customevaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent:chloroform-methanol)

Sources & evidence

ORD record
ord-f876bcd450bd467ca01a7d769451e4be
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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