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Hydrochloric Acid → 4-((3,3-Dimethylcyclobutyl)(quinolin-3-ylamino)methyl)benzoic acid

HRID 1424272
Notes
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Reaction equation

HRID 1424272 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:5][CH:4]([CH:6]([NH:18][C:19]2[CH:20]=[N:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13]CC)=[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([CH3:29])[CH2:5][CH:4]([CH:6]([NH:18][C:19]2[CH:20]=[N:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:7]2[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:16][CH:17]=2)[CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71239295Ethyl 4-((3,3-dimethylcyclobutyl)(quinolin-3-ylamino) methyl)benzoate

Product 1

HCID 712393444-((3,3-Dimethylcyclobutyl)(quinolin-3-ylamino)methyl)benzoic acidYield 93%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing ethyl 4-((3,3-dimethylcyclobutyl)(quinolin-3-ylamino)methyl)benzoate (17.0 mg, 0.0440 mmol) was added tetrahydrofuran (0.110 mL), methanol (0.110 mL), and 1 N sodium hydroxide (0.110 mL, 0.110 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 (0.110 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 4-((3,3-dimethylcyclobutyl)(quinolin-3-ylamino)methyl)benzoic acid; (14.8 mg, 93% yield) as a solid. 1H NMR (400 MHz, CDCl3) δ: 8.67 (br. s., 1H), 8.06 (d, J=8.2 Hz, 2H), 7.96 (d, J=7.4 Hz, 1H), 7.48 (d, J=8.4 Hz, 2H), 7.46-7.32 (m, 3H), 6.76 (d, J=2.5 Hz, 1H), 4.30 (d, J=9.4 Hz, 1H), 2.62-2.50 (m, 1H), 2.10-1.98 (m, 1H), 1.80-1.69 (m, 2H), 1.69-1.58 (m, 1H), 1.14 (s, 3H), 1.09 (s, 3H). MS (M+1): 361.2.

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-64f325404f11428ea8fb928e154879c3
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927577B2

Reaction notes

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