Hydrochloric Acid → HCID 59321498, compound

HRID 2423465Notes

Reaction equation

HRID 2423465 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]([CH2:16][C:17]1[C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[C:32]4[C:37](=[CH:38][CH:39]=3)[N:36]=[C:35]([C:40]([O:42]C)=[O:41])[CH:34]=[CH:33]4)=[CH:26][CH:25]=2)=[C:20]([CH:44]([CH3:46])[CH3:45])[O:19][N:18]=1)C(=O)C(F)(F)F.O1CCCC1.[OH-].[Na+].Cl>O.CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][CH2:16][C:17]1[C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:31]=[C:32]4[C:37](=[CH:38][CH:39]=3)[N:36]=[C:35]([C:40]([OH:42])=[O:41])[CH:34]=[CH:33]4)=[CH:26][CH:25]=2)=[C:20]([CH:44]([CH3:46])[CH3:45])[O:19][N:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59321544Methyl 6-[4-({[3-{[(2,6-dichlorophenyl)(trifluoroacetyl)amino]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate

Product 1

HCID 59321498HCID 59321498, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 6-[4-({[3-{[(2,6-dichlorophenyl)(trifluoroacetyl)amino]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylate (10 mg, 0.015 mmol) in 1:1 tetrahydrofuran:methanol (0.75 mL) was added 1 N sodium hydroxide (0.37 mL, 0.37 mmol). The solution was heated in a microwave reactor at 90° C. for 10 minutes. The solution was concentrated and the residue was taken up with ethyl acetate. Then 1 N hydrochloric acid (0.37 mL, 0.37 mmol) was added followed by water. The layers were separated and the aqueous layer was extracted one more time with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated to afford 6-[4-({[3-{[(2,6-dichlorophenyl)amino]methyl}-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-2-quinolinecarboxylic acid (8 mg, 100%). 1H-NMR (400 MHz, CDCl3) δ 8.46 (d, J=9 Hz, 1H), 8.31-8.24 (m, 2H), 8.11-8.07 (m, 2H), 7.69 (d, J=9 Hz, 2H), 7.25-7.20 (m, 2H), 7.07 (d, J=9 Hz, 2H), 6.84-6.80 (m, 1H), 4.96 (s, 2H), 4.60 (s, 2H), 3.24 (septet, J=7 Hz, 1H), 1.36 (d, J=7 Hz, 6H). HRMS (ESI) C30H25Cl2N3O4 calculated: 562.1300 (M+H)+, found: 562.1292 (M+H)+.

Workup

  1. concentrationThe solution was concentrated
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted one more time with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-422f5dfe447949ce8b7348c7b1e1e8bc
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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