Hydrochloric Acid → HCID 59321565, compound

HRID 2423496Notes

Reaction equation

HRID 2423496 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[C:26]([C:31]([O:33]C)=[O:32])[CH:25]=[CH:24]5)=[CH:17][CH:16]=3)=[C:11]([CH:35]([CH3:37])[CH3:36])[O:10][N:9]=2)=[C:6]([CH3:38])[CH:5]=[CH:4][N:3]=1.CO.[OH-].[Na+].Cl>C1COCC1>[CH3:1][C:2]1[C:7]([C:8]2[C:12]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[C:26]([C:31]([OH:33])=[O:32])[CH:25]=[CH:24]5)=[CH:17][CH:16]=3)=[C:11]([CH:35]([CH3:36])[CH3:37])[O:10][N:9]=2)=[C:6]([CH3:38])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59321552HCID 59321552, compound

Product 1

HCID 59321565HCID 59321565, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 6-[4-({[3-(2,4-dimethyl-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (20 mg, 0.04 mmol) in THF (0.4 mL) was placed in a microwave reaction tube followed by methanol (0.20 mL) followed by a 1 N solution of sodium hydroxide (0.08 mL, 0.08 mmol). The tube was sealed and heated to 100° C. for 10 minutes. The solution was neutralized with 1 N HCl and concentrated. The residue was diluted with water and filtered. The resulting solid was dried with P2O5 in a 45° C. vacuum oven under reduced pressure to yield 6-[4-({[3-(2,4-dimethyl-3-pyridinyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (17 mg, 86%). 1H NMR (400 MHz, DMSO-d6): δ 13.5-13.2 (br s, 1H), 8.53 (d, J=9 Hz, 1H), 8.38 (d, J=5 Hz, 1H), 8.27 (s, 1H), 8.17-8.08 (m, 3H), 7.74 (d, J=9 Hz, 2H), 7.22 (d, J=5 Hz, 1H), 7.22 (d, J=9 Hz, 2H), 4.79 (s, 2H), 3.47 (septet, J=7 Hz, 1H), 2.24 (s, 3H), 2.08 (s, 3H), 1.33 (d, J=7 Hz, 6H). ESI-LCMS m/z 494 (M+H)+.

Workup

  1. customThe tube was sealed
  2. concentrationconcentrated
  3. additionThe residue was diluted with water
  4. filtrationfiltered
  5. dry with materialThe resulting solid was dried with P2O5 in a 45° C. vacuum oven under reduced pressure

Sources & evidence

ORD record
ord-bc4de50daacf44ed9781c46975fb86ff
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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