Lithium hydroxide, monohydrate → 3-[[[4-(2-Amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]cyclohexanecarboxylic acid

HRID 1353471Notes

Reaction equation

HRID 1353471 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([O:29]C)=[O:28])[CH2:22]3)=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:31])=[CH:7][CH:8]=2)[N:3]=1.O[Li].O>C1COCC1.O>[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]([NH:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH:23]([C:27]([OH:29])=[O:28])[CH2:22]3)=[O:19])[CH2:16][CH2:17]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:31])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86591808HCID 86591808, compound

Product 1

HCID 211015923-[[[4-(2-Amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]cyclohexanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]-cyclohexanecarboxylic acid, methyl ester (150 mg, 0.33 mmol) in THF (20 mL) and water (6 mL) was added LiOH.H2O (28.0 mg). The reaction mixture was stirred at rt overnight, and then solvent was evaporated in vacuo. The resulting residue was acidified to pH 4, the precipitate was collected by filtration and dried to afford the title product. LC-MS: 432 (M++1). 1H NMR (DMSO-d6) δ 1.10 (m, 2H), 1.25 (m, 2H), 1.75 (m, 3H), 1.95 (m, 1H), 2.25 (m, 1H), 3.10 (m, 4H), 3.50 (m, 5H), 6.25 (s, 1H), 6.40 (d, 1H), 7.25 (m, 1H), 7.50 (s, 1H), 780 (d, 1H).

Workup

  1. customsolvent was evaporated in vacuo
  2. filtrationthe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-85136c37e098488180db8b9031c5cbc8
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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