Potassium Carbonate → HCID 68295230, compound

HRID 572494Notes

Reaction equation

HRID 572494 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH:4]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:5]1[N:6]([CH3:28])[C:7](=[O:27])[C:8]2[C:13]([C:14]=1[C:15]1[C:16]([CH3:25])=[C:17]3[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=[C:10]([OH:26])[CH:9]=2.C([O-])([O-])=O.[K+].[K+].BrC[CH2:43][CH2:44][OH:45]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:34])[CH:4]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])[C:5]1[N:6]([CH3:28])[C:7](=[O:27])[C:8]2[C:13]([C:14]=1[C:15]1[C:16]([CH3:25])=[C:17]3[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=[C:10]([O:26][CH2:43][CH2:44][OH:45])[CH:9]=2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 68295156HCID 68295156, compound

Product 1

HCID 68295230HCID 68295230, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-Butoxy-[7-hydroxy-2-methyl-4-(5-methyl-chroman-6-yl)-1-oxo-1,2-dihydro-isoquinolin-3-yl]-acetic acid methyl ester (50 mg, 0.17 mmol) in DMF (1 ml) was added K2CO3 (44.5 mg, 0.322 mmol) and 3-bromopropan-1-ol (40.3 mg, 0.322 mmol) at RT. The resultant mixture was stirred at 70° C. for 3 hr. The reaction mixture was diluted with water and extracted with EA (10 mL*3), dried over sodium sulfate and concentrated to dryness. The mixture was purified by Pre-TLC to afford the title product (30 mg, 55%). LCMS (10-80 AB—2MIN.M): Rt=1.223, purity=93.7%, M+1=510.

Workup

  1. extractionextracted with EA (10 mL*3)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe mixture was purified by Pre-TLC

Sources & evidence

ORD record
ord-d7fb3e411d064757aa794ebe33d8b017
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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