Hydrochloric Acid → HCID 58902304, compound

HRID 1640197Notes

Reaction equation

HRID 1640197 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:12])[NH:7]2.[OH:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][CH:20]([C:24]([OH:26])=[O:25])[CH2:21]2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C.O>[O:12]=[C:6]1[NH:7][C:8]2[N:9]=[CH:10][CH:11]=[C:2]([O:13][C:14]3[CH:23]=[C:22]4[C:17]([CH2:18][CH2:19][CH:20]([C:24]([OH:26])=[O:25])[CH2:21]4)=[CH:16][CH:15]=3)[C:3]=2[CH:4]=[CH:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 106074825-chloro-1,8-naphthyridin-2(1H)-oneHCID 145412687-Hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 58902304HCID 58902304, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of 5-chloro-1,8-naphthyridin-2(1H)-one (0.050 g, 0.00028 mol), 7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (0.080 g, 0.00042 mol), and cesium carbonate (0.270 g, 0.000829 mol) in DMF (1 mL) was subjected to microwave heating (180° C.) for 15 min. The reaction mixture was dissolved in water and then acidified to pH of 2 with 1N HCl. The mixture was extracted with EtOAc (4×). The combined organic solutions were dried over MgSO4, filtered, and concentrated. The residue was triturated with DCM and hexanes to produce 7-[(7-oxo-7,8-dihydro-1,8-naphthyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid as a white solid (0.066 g, 71%). LCMS: (FA) ES+ 337.3.

Workup

  1. extractionThe mixture was extracted with EtOAc (4×)
  2. dry with materialThe combined organic solutions were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was triturated with DCM and hexanes

Sources & evidence

ORD record
ord-75e6d1fa399b4847aaeed460ceea5c9f
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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