HCID 123135825, compound → HCID 117667711, compound

HRID 712675Notes

Reaction equation

HRID 712675 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([CH:24]=[CH:25][CH2:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:23]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([CH2:24][CH2:25][CH2:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:23]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 123135825HCID 123135825, compound

Product 1

HCID 117667711HCID 117667711, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5% Pd on carbon (150 mg, 0.07 mmol) is added to a solution of 6-[5-(-3-methanesulfonyl-propenyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (340 mg, 0.79 mmol) in MeOH (30 mL). The mixture is stirred at room temperature under H2 atmosphere of 40 PSI for 16 hrs. After filtration, the filtrate is concentrated to give 240 mg of 6-[5-(3-methanesulfonyl-propyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester. This is then used to prepare 6-[5-(3-methanesulfonyl-propyl)-pyridin-3-yl]-1,2,3,4-tetrahydro-[1,8]naphthyridine according to the procedure for Step 2 of Example 27 using 20% trifluoroacetic acid in DCM as the reagent.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-0d26dc422a8d4d7c85158e2ffd9517a3
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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