Sodium Bicarbonate → N-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-fluoro-nicotinamide

HRID 888165Notes

Reaction equation

HRID 888165 reaction equation
[F:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]1[CH:21]=[C:20]2[C:15]([C:16]([CH3:24])([CH3:23])[CH2:17][NH:18][C:19]2=[O:22])=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:23][C:16]1([CH3:24])[C:15]2[C:20](=[CH:21][C:12]([NH:11][C:4](=[O:5])[C:3]3[CH:7]=[CH:8][CH:9]=[N:10][C:2]=3[F:1])=[CH:13][CH:14]=2)[C:19](=[O:22])[NH:18][CH2:17]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 219595822-Fluoropyridine-3-carbonyl chlorideHCID 219596427-Amino-4,4-dimethyl-3,4-dihydroisoquinolin-1(2h)-one

Product 1

HCID 21959600N-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-7-yl)-2-fluoro-nicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-fluoro-nicotinoyl chloride (283 mg, 1.79 mmol) and 7-amino-4,4-dimethyl-3,4-dihydro-2H-isoquinolin-1-one (340 mg, 1.79 mmol) in CH2Cl2 (10 mL) was added NaHCO3 (573 mg, 7.16 mmol). The resulting mixture was stirred for 30 min at RT and filtered. The filtrate was concentrated and purified on silica gel column to yield the title compound as white solid. MS (ES+): 314 (M+H)+. Calc'd for C17H16FN3O2—313.12

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified on silica gel column

Sources & evidence

ORD record
ord-55e2c9d3c17f49668799566c074a3b56
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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