1,1'-Carbonyldiimidazole → (Quinolin-4-yl)-carbamic acid 2-(6,7-dimethoxy-1-phenethyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester

HRID 2414829Notes

Reaction equation

HRID 2414829 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:8]([CH2:23][CH2:24][OH:25])[CH2:7][CH2:6]2.C1N=CN([C:31]([N:33]2C=N[CH:35]=[CH:34]2)=[O:32])C=1.N[C:39]1[C:48]2[C:43](=[CH:44]C=C[CH:47]=2)[N:42]=[CH:41][CH:40]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.O.CC(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[N:8]([CH2:23][CH2:24][O:25][C:31](=[O:32])[NH:33][C:34]1[C:35]3[C:41](=[CH:40][CH:39]=[CH:48][CH:47]=3)[N:42]=[CH:43][CH:44]=1)[CH2:7][CH2:6]2

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 684764-AminoquinolineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 22643310HCID 22643310, compound

Product 1

HCID 10118419(Quinolin-4-yl)-carbamic acid 2-(6,7-dimethoxy-1-phenethyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

To a solution of 2-(6,7-dimethoxy-1-phenethyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethanol (example 113.1, 29.7 mg, 0.087 mmol) in THF (1 mL) is added CDI (28.2 mg, 0.174 mmol, 2.0 eq). The reaction mixture is stirred at rt for 3 h, and then 4-amino-quinoline (example C3, 14 mg, 0.1 mmol) is added. To the resulting solution is added in a single portion NaHMDS (2 M in THF, 218 μL, 0.44 mmol). The reaction mixture is stirred at rt for 30 min, then H2O/AcOH (9:1, 0.4 mL) is added. The reaction mixture is evaporated and the residue purified by preparative HPLC to provide the title compound.

Workup

  1. stirringThe reaction mixture is stirred at rt for 30 min
  2. customThe reaction mixture is evaporated
  3. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-70f50c4162744de9bd1bdc3258f47337
Source dataset
uspto-grants-2004_11
Patent number
US06815451B2

Reaction notes

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