Dimethylformamide → HCID 68450072, compound

HRID 1747093Notes

Reaction equation

HRID 1747093 reaction equation
C([CH:8]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH2:20][NH:21][C:22]([CH:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27](=[O:34])[N:26]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]3[NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[CH:25]2[C:46]2[CH:51]=[CH:50][C:49]([Cl:52])=[CH:48][C:47]=2[Cl:53])=[O:23])[N:14]=1)[C:9]([O-:11])=[O:10])C1C=CC=CC=1.CN(C=O)C>[Pd].C(O)C>[Cl:53][C:47]1[CH:48]=[C:49]([Cl:52])[CH:50]=[CH:51][C:46]=1[CH:25]1[CH:24]([C:22]([NH:21][CH2:20][CH2:19][C:15]2[N:14]=[C:13]([O:12][CH2:8][C:9]([OH:11])=[O:10])[CH:18]=[CH:17][CH:16]=2)=[O:23])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=[O:34])[N:26]1[CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH:36]1[NH:41][S:42]([CH3:45])(=[O:43])=[O:44]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 131733555HCID 131733555, 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-28709c061ff4427e8f86d8c28f999bb9
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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