Potassium Carbonate → HCID 58476255, compound

HRID 1801185Notes

Reaction equation

HRID 1801185 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=3)[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:23]([N:30]1[CH2:39][CH2:38][C:37]2[C:36](=[O:40])[NH:35][CH:34]=[N:33][C:32]=2[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH2:23]([N:30]1[CH2:39][CH2:38][C:37]2[C:36](=[O:40])[N:35]([C:2]3[CH:3]=[C:4]([CH:8]4[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]5[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=5)[NH:9]4)[CH:5]=[CH:6][CH:7]=3)[CH:34]=[N:33][C:32]=2[CH2:31]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 584761942-(3-Bromophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidHCID 1357235075,6,7,8-Tetrahydro-7-(phenylmethyl)pyrido(3,4-d)pyrimidin-4(3H)-one

Product 1

HCID 58476255HCID 58476255, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (360 mg, 1.0 mmol), 7-benzyl-5,6,7,8-tetrahydro-3H-pyrido[3,4-d]pyrimidin-4-one (300 mg, 1.3 mmol), copper(I) iodide (80 mg, 0.4 mmol), N,N-dimethylglycine hydrochloride (117 mg, 0.8 mmol) and potassium carbonate (769 mg, 5.6 mmol) in dimethyl sulfoxide (5 mL) was stirred at 120° C. for 16 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2×150 mL), washed with water (2×50 mL) and saturated aqueous ammonium chloride solution (2×50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-[3-(7-benzyl-4-oxo-5,6,7,8-tetrahydro-4H-pyrido[3,4-d]pyrimidin-3-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (320 mg, 61%) as a white solid: LC/MS m/e calcd for C32H32N4O3 (M+H)+: 521.64, observed: 521.2.

Workup

  1. temperatureThen the reaction mixture cooled to room temperature
  2. extractionThe reaction mixture was extracted with ethyl acetate (2×150 mL)
  3. washwashed with water (2×50 mL) and saturated aqueous ammonium chloride solution (2×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water)

Sources & evidence

ORD record
ord-5420bf9105314af5a360765e8242e442
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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