Ethyl Acetate → HCID 59478297, compound

HRID 1747099Notes

Reaction equation

HRID 1747099 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([NH:14][C:15]([C@@H:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20](=[O:27])[N:19]([C@H:28]3[CH2:33][CH2:32][CH2:31][CH2:30][C@@H:29]3[NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[C@H:18]2[C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][C:40]=2[Cl:46])=[O:16])[CH3:13])[N+:7]=1[O-:47])(=O)C.O.NN.C(OCC)(=O)C>CO>[Cl:46][C:40]1[CH:41]=[C:42]([Cl:45])[CH:43]=[CH:44][C:39]=1[C@H:18]1[C@H:17]([C:15]([NH:14][CH:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][OH:4])[N+:7]=2[O-:47])[CH3:13])=[O:16])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[N:19]1[C@H:28]1[CH2:33][CH2:32][CH2:31][CH2:30][C@@H:29]1[NH:34][S:35]([CH3:38])(=[O:36])=[O:37]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 59478310HCID 59478310, compound

Product 1

HCID 59478297HCID 59478297, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 777 mg of {6-[1-({[(3R,4R)-3-(2,4-dichlorophenyl)-2-{(1S,2S)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl]carbonyl}amino)ethyl]-1-oxidopyridin-2-yl}methyl acetate in 17 ml of methanol was added 0.21 ml of hydrazine monohydrate, followed by stirring for one week. Ethyl acetate was added thereto, followed by stirring for a while and concentrating, and the residue was purified by silica gel column chromatography (eluent:chloroform-methanol). Ethyl acetate and diisopropyl ether were used to make a powder, thereby obtaining 501 mg of (3R,4R)-3-(2,4-dichlorophenyl)-N-{1-[6-(hydroxymethyl)-1-oxidopyridin-2-yl]ethyl}-2-{(1S,2S)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide as a colorless solid.

Workup

  1. stirringby stirring for a while
  2. concentrationconcentrating
  3. customthe residue was purified by silica gel column chromatography (eluent:chloroform-methanol)

Sources & evidence

ORD record
ord-2a95b6d854f041e9bc99b8c165ba7740
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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