2-Dimethylaminopyridine → HCID 21192928, compound

HRID 1067293Notes

Reaction equation

HRID 1067293 reaction equation
[C:1](OC=O)(=[O:3])C.[Cl:7][C:8]1[C:9]([NH:18][C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=2)=[CH:10][CH:11]=[C:12]2[C:17]=1[CH2:16][NH:15][CH2:14][CH2:13]2.CN(C1C=CC=CN=1)C>ClCCl>[CH:1]([N:15]1[CH2:14][CH2:13][C:12]2[C:17](=[C:8]([Cl:7])[C:9]([NH:18][C:19](=[O:32])[C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([C:28]([F:29])([F:30])[F:31])[CH:21]=3)=[CH:10][CH:11]=2)[CH2:16]1)=[O:3]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 75269Acetic-formic anhydrideHCID 21192910HCID 21192910, compound

Product 1

HCID 21192928HCID 21192928, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formic acetic anhydride (0.21 g) was added to N-(8-chloro-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-methoxy-3-trifluoromethylbenzamide (0.15 g) and dimethylaminopyridine (0.05 g) in dichloromethane. The mixture was stirred at room temperature overnight and quenched with saturated aqueous sodium hydrogen carbonate (20 ml). The organic phase was separated and washed with brine, dried (MgSO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, ammonia/methanol/dichloromethane mixtures as eluant) to give the title compound (0.10 g)

Workup

  1. customquenched with saturated aqueous sodium hydrogen carbonate (20 ml)
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4) and solvent
  5. customremoved at reduced pressure
  6. customchromatographed (silica gel, ammonia/methanol/dichloromethane mixtures as eluant)

Sources & evidence

ORD record
ord-c90ef3258dd046acbac016b352f13b0a
Source dataset
uspto-grants-2001_06
Patent number
US06248754B1

Reaction notes

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