Potassium Carbonate → HCID 59190847, compound

HRID 418337Notes

Reaction equation

HRID 418337 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16](=[O:28])[NH:17][C:18]2[CH:27]=[C:26]3[C:21]([CH2:22][CH2:23][NH:24][CH2:25]3)=[CH:20][CH:19]=2)[CH:11]=1)=[O:7].Br[CH2:35][C:36]([O:38][CH3:39])=[O:37].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:39][O:38][C:36](=[O:37])[CH2:35][N:24]1[CH2:23][CH2:22][C:21]2[C:26](=[CH:27][C:18]([NH:17][C:16](=[O:28])[C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]4[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:11]=3)=[CH:19][CH:20]=2)[CH2:25]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 25057409Benzamide, 3,4-dimethoxy-N-[[3-[[(1,2,3,4-tetrahydro-7-isoquinolinyl)amino]carbonyl]phenyl]methyl]-

Product 1

HCID 59190847HCID 59190847, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolved 3,4-dimethoxy-N-[3-(1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide (50.0 mg, 0.12 mmol) in 1 mL of DMF. To the mixture was added methyl bromoacetate (0.02 mL, 0.20 mmol) and K2CO3 (50 mg, 0.36 mmol). The mixture was stirred at room temperature overnight. LC-MS indicated the desired product. Dissolved in 5 mL of DMF and purified via prep HPLC (5%-95% CH3CN/H2O) to give 37 mg (7-{3-[(3,4-dimethoxy-benzoylamino)-methyl]-benzoylamino}-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid methyl ester. MS, electrospray 590.6 (M+H).

Sources & evidence

ORD record
ord-599b937efbeb48758c010a0128709fbd
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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