Acetic Acid → N-[3-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-3,4-dimethoxy-benzamide

HRID 418334Notes

Reaction equation

HRID 418334 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:29])[NH:18][C:19]2[CH:28]=[C:27]3[C:22]([CH2:23][CH2:24][NH:25][CH2:26]3)=[CH:21][CH:20]=2)[CH:12]=1)=[O:8].CC(O)=O.[CH:39](=O)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[CH2:39]([N:25]1[CH2:24][CH2:23][C:22]2[C:27](=[CH:28][C:19]([NH:18][C:17]([C:13]3[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=3)[CH2:10][NH:9][C:7](=[O:8])[C:6]3[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:4]([O:3][CH3:2])[CH:5]=3)=[O:29])=[CH:20][CH:21]=2)[CH2:26]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66649515HCID 66649515, compound

Product 1

HCID 25055846N-[3-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-3,4-dimethoxy-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Suspended 3,4-Dimethoxy-N-[3-(1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide hydrochloride (50.0 mg, 0.104 mmol) in 2 mL of THF. To this was added AcOH (0.06 mL, 1.0 mmol) and benzaldehyde (0.016 mL, 0.150 mmol). The mixture stirred for 1 h. To this was added NaBH(OAc)3 (63.3 mg, 0.300 mmol). The mixture stirred for 50 h. LC-MS analysis indicated the desired product. Concentrated the mixture to dryness. Redissolved in CH2Cl2/MeOH and applied to a SiO2 prep plate. Eluted with (10% MeOH/1% NH3/CH2Cl2) to give 40.6 mg of N-[3-(2-Benzyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-3,4-dimethoxy-benzamide. MS, electrospray 536.4 (M+H).

Workup

  1. stirringThe mixture stirred for 50 h

Sources & evidence

ORD record
ord-0f3071c77e84468c8a2ecf8fe823344e
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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