Hydrochloric Acid → HCID 20714285, compound

HRID 2270100Notes

Reaction equation

HRID 2270100 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:37])[C:7]=1[NH:8][C:9]([C:11]1[C:20](=[O:21])[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C@H:22]2[CH2:26][CH2:25][N:24](C(OCC3C=CC=CC=3)=O)[CH2:23]2)[CH:12]=1)=[O:10].Cl>[Pd].CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:37])[C:7]=1[NH:8][C:9]([C:11]1[C:20](=[O:21])[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C@H:22]2[CH2:26][CH2:25][NH:24][CH2:23]2)[CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15908296HCID 15908296, compound

Product 1

HCID 20714285HCID 20714285, compoundYield 193.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 4 ml methanol solution of 60 mg (0.11 mmol) of the compound obtained in Example 10, 20 μl (0.12 mmol) of 6N-hydrochloric acid and 30 mg of 10% palladium activated carbon were added and stirred at room temperature for 21 hours under hydrogen atmosphere. Then, after the catalyst was removed by filtration, the mother liquor was concentrated to obtain 47 mg of (S)-N-(3,5-dichloropyridin-4-yl)-1-(3-pyrrolidyl)-1,4-dihydro[1,8]naphthyridin-4-one-3-carboxamide hydrochloride, as a colorless oily substance.

Workup

  1. customThen, after the catalyst was removed by filtration
  2. concentrationthe mother liquor was concentrated

Sources & evidence

ORD record
ord-4619b1577a0341379a456bb9031648c5
Source dataset
uspto-grants-2001_12
Patent number
US06331548B1

Reaction notes

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