Water → HCID 136018627, compound

HRID 2053453Notes

Reaction equation

HRID 2053453 reaction equation
C([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C:11]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[C:10]([C:25]2[O:29][N:28]=[C:27]([CH3:30])[CH:26]=2)[C:9]1=[O:31])C1C=CC=CC=1.O.[OH-].[Na+]>CS(O)(=O)=O>[Cl:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[NH:8][C:9](=[O:31])[C:10]([C:25]1[O:29][N:28]=[C:27]([CH3:30])[CH:26]=1)=[C:11]2[N:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59655017HCID 59655017, compound

Product 1

HCID 136018627HCID 136018627, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 1-benzyl-6-chloro-3-(3-methyl-isoxazol-5-yl)-4-piperidin-1-yl-1H-quinolin-2-one (21 mg, 0.048 mmol) in 1 mL of CH3SO3H was stirred at 110° C. for 8 h, then cooled to rt. Treated with 20 mL of H2O, the mixture was neutralized to pH=7 with 2N NaOH solution and extracted with EtOAc (2×30 ml). The combined organic layers were washed with H2O (10 ml), brine (10 ml) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (20-40% EtOAc/DCM) gave 4.5 mg (27%) of product as a yellow solild: 1H-NMR (CDCl3; 400 MHz) δ 10.9 (s, 1H), 7.83 (d, 1H, J=2.2 Hz), 7.45 (dd, 1H, J=8.6, 2.2 Hz), 7.18 (d, 1H, J=8.6 Hz), 6.50 (s, 1H), 3.00 (br s, 4H), 2.42 (s, 3H), 1.62-1.78 (m, 6H). Mass spectrum (ESI, m/z): Calcd. for C18H18ClN3O2, 344.1 (M+H), found 344.1.

Workup

  1. extractionextracted with EtOAc (2×30 ml)
  2. washThe combined organic layers were washed with H2O (10 ml), brine (10 ml)
  3. dry with materialdried (Na2SO4)
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-004f15c1cad5479cbb17f7f077ab562b
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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