Dimethylformamide → HCID 68450072, compound

HRID 450820Notes

Reaction equation

HRID 450820 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]2[N:29]=[C:28]([O:30][CH2:31][C:32]([O:34]CC3C=CC=CC=3)=[O:33])[CH:27]=[CH:26][CH:25]=2)=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:42])[N:10]1[CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH:44]1[NH:49][S:50]([CH3:53])(=[O:52])=[O:51].CN(C=O)C>[Pd].C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH:18]([C:19]([NH:21][CH2:22][CH2:23][C:24]2[N:29]=[C:28]([O:30][CH2:31][C:32]([OH:34])=[O:33])[CH:27]=[CH:26][CH:25]=2)=[O:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:42])[N:10]1[CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH:44]1[NH:49][S:50]([CH3:53])(=[O:51])=[O:52]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 72303410HCID 72303410, compound

Product 1

HCID 68450072HCID 68450072, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixed liquid of 420 mg of benzyl ({6-[2-({[(3RS,4RS)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl]carbonyl}amino)ethyl]pyridin-2-yl}oxy)acetate, 5 ml of DMF, and 5 ml of ethanol was added 84 mg of 5% palladium/carbon, followed by stirring at room temperature for 15 minutes under a hydrogen atmosphere. After separating the palladium/carbon by filtration, the solvent was evaporated, and the residue was purified by silica gel column chromatography (eluent: chloroform-methanol) to obtain 78 mg of ({6-[2-({[(3RS,4RS)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(methylsulfonyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl]carbonyl}amino)ethyl]pyridin-2-yl}oxy)acetic acid as a white solid.

Workup

  1. customAfter separating the palladium/carbon
  2. filtrationby filtration
  3. customthe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography (eluent: chloroform-methanol)

Sources & evidence

ORD record
ord-d89cbb9166ca4e729eab019bcdd9c238
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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