Methanol → HCID 59321533, compound

HRID 2423473Notes

Reaction equation

HRID 2423473 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([CH2:12][C:13]1[C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:27]=[C:28]4[C:33](=[CH:34][CH:35]=3)[N:32]=[C:31]([C:36]([O:38]CC)=[O:37])[CH:30]=[CH:29]4)=[CH:22][CH:21]=2)=[C:16]([CH:41]([CH3:43])[CH3:42])[O:15][N:14]=1)(=[O:11])=[O:10].O1CCCC1.CO.[OH-].[Na+]>ClCCl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[S:9]([CH2:12][C:13]1[C:17]([CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:27]=[C:28]4[C:33](=[CH:34][CH:35]=3)[N:32]=[C:31]([C:36]([OH:38])=[O:37])[CH:30]=[CH:29]4)=[CH:24][CH:25]=2)=[C:16]([CH:41]([CH3:43])[CH3:42])[O:15][N:14]=1)(=[O:10])=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321485HCID 59321485, compound

Product 1

HCID 59321533HCID 59321533, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of ethyl 6-[4-({[3-{[(2,6-dichlorophenyl)sulfonyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (4 mg, 0.006 mmol) in 1:1 tetrahydrofuran:methanol (0.5 mL) was added 1 N sodium hydroxide (0.020 mL, 0.020 mmol). The solution was heated in a microwave reactor at 75° C. for approximately 10 minutes. Then the mixture was diluted with dichloromethane and 1 N hydrochloric (0.020 mL, 0.020 mmol) was added. The solution was washed with water, dried over magnesium sulfate and concentrated to afford 6-[4-({[3-{[(2,6-dichlorophenyl)sulfonyl]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (1 mg, 25%). 1H-NMR (400 MHz, CDCl3) δ 8.44 (d, J=8 Hz, 1H), 8.29 (d, J=8 Hz, 1H), 8.21 (d, J=8 Hz, 1H), 8.10-8.07 (m, 2H), 7.71 (d, J=8 Hz, 2H), 7.47-7.38 (m, 3H), 7.12 (d, J=8 Hz, 2H), 5.16 (s, 2H), 4.86 (s, 2H), 3.25 (septet, J=7 Hz, 1H), 1.34 (d, J=7 Hz, 6H). LRMS m/z 609 [M−H]−.

Workup

  1. additionwas added
  2. washThe solution was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b28fd9da731c4637b806e6121e4ca347
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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