Water → HCID 178487606, compound

HRID 2202331Notes

Reaction equation

HRID 2202331 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]1[CH:11]=[C:12]([NH:21][C:22]([C@@H:24]2[N:33]([C:34]([C@@H:36]3[CH2:39][C@H:38]([CH2:40][C:41]([OH:43])=[O:42])[CH2:37]3)=[O:35])[CH2:32][CH2:31][C:30]3[N:29]=[C:28]([O:44][CH3:45])[CH:27]=[CH:26][C:25]2=3)=[O:23])[CH:13]=[C:14]2[C:18]=1[C:17]([CH3:20])([CH3:19])[CH2:16][CH2:15]2.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[F:9][C:10]1[CH:11]=[C:12]([NH:21][C:22]([C@@H:24]2[N:33]([C:34]([C@@H:36]3[CH2:39][C@H:38]([CH2:40][C:41]([O:43][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:42])[CH2:37]3)=[O:35])[CH2:32][CH2:31][C:30]3[N:29]=[C:28]([O:44][CH3:45])[CH:27]=[CH:26][C:25]2=3)=[O:23])[CH:13]=[C:14]2[C:18]=1[C:17]([CH3:20])([CH3:19])[CH2:16][CH2:15]2

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178487600HCID 178487600, compound

Product 1

HCID 178487606HCID 178487606, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Benzyl bromide (84 μL, 0.71 mmol) was added to a mixture of (cis-3-(((5R)-5-((7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)carbamoyl)-2-methoxy-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)carbonyl)cyclobutyl)acetic acid (300 mg, 0.59 mmol) and potassium carbonate (98 mg, 0.71 mmol) in DMF (5 mL) at room temperature, and the mixture was stirred at room temperature for 2.5 hr. To the reaction mixture was added water (60 mL), and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent so gradient; 20→41% ethyl acetate/hexane) to give the title compound (282.3 mg, 0.471 mmol, 80%) as a colorless amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (×3)
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent so gradient

Sources & evidence

ORD record
ord-8a12bd008a1a49aea22f726294b61cf6
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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