Hydrochloric Acid → HCID 71239656, compound

HRID 2281164Notes

Reaction equation

HRID 2281164 reaction equation
[CH3:1][C:2]1([CH3:35])[CH2:5][CH:4]([CH:6]([NH:23][C:24]2[CH:25]=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[C:29]([F:34])[CH:28]=3)[C:7]2[CH:22]=[CH:21][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.O1CCCC1.[OH-].[Na+].Cl>C(OCC)(=O)C.O.CO>[CH3:1][C:2]1([CH3:35])[CH2:5][CH:4]([CH:6]([NH:23][C:24]2[CH:25]=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[C:29]([F:34])[CH:28]=3)[C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:12])=[CH:21][CH:22]=2)[CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71239511HCID 71239511, compound

Product 1

HCID 71239656HCID 71239656, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing ethyl 3-(4-((3,3-dimethylcyclobutyl)(7-fluoroquinolin-3-ylamino)methyl)benzamido)propanoate (6.20 mg, 0.0130 mmol) was added tetrahydrofuran (0.0330 mL), methanol (0.0330 mL), and 1 N sodium hydroxide (0.0330 mL, 0.0330 mmol). The reaction was stirred for 18 h at room temperature. The reaction was then diluted with ethyl acetate and water. 1 N hydrochloric acid (0.0330 mL) was then added dropwise to bring the pH to 3. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered, and concentrated to provide 3-(4-((3,3-dimethylcyclobutyl)(7-fluoroquinolin-3-ylamino)methyl)benzamido)propanoic acid (3.5 mg, 60% yield) as a solid. 1H NMR (400 MHz, CD3OD, δ): 8.53 (d, J=2.7 Hz, 1H), 8.45 (t, J=5.7 Hz, 1H), 7.80-7.72 (m, 2H), 7.59-7.51 (m, 3H), 7.43 (dd, J=10.0, 2.6 Hz, 1H), 7.23 (td, J=8.8, 2.5 Hz, 1H), 6.99 (d, J=2.5 Hz, 1H), 4.38 (d, J=9.6 Hz, 1H), 3.67-3.57 (m, 2H), 2.67-2.60 (m, 3H), 2.16-2.06 (m, 1H), 1.78 (d, J=2.5 Hz, 2H), 1.63-1.52 (m, 1H), 1.18 (s, 3H), 1.13 (s, 3H). (M+1): 450.3.

Workup

  1. extractionThe aqueous layer was extracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6a2b6a1a63b746779614dde1a21fd965
Source dataset
uspto-grants-2015_09
Patent number
US09139538B2

Reaction notes

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