Lithium hydroxide, monohydrate → HCID 178524387, compound

HRID 1093739Notes

Reaction equation

HRID 1093739 reaction equation
O[Li].O.C[O:5][C:6](=[O:37])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:36])[CH2:21][NH:22][C:23]([C:25]3[CH:29]=[C:28]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[NH:27][N:26]=3)=[O:24])[CH2:16][CH2:15]2)[CH:8]=1>CO.O>[C:30]1([C:28]2[NH:27][N:26]=[C:25]([C:23]([NH:22][CH2:21][C:20]([N:17]3[CH2:16][CH2:15][CH:14]([O:13][C:9]4[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=4)[C:6]([OH:37])=[O:5])[CH2:19][CH2:18]3)=[O:36])=[O:24])[CH:29]=2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178497959HCID 178497959, compound

Product 1

HCID 178524387HCID 178524387, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

LiOH.H2O (44 mg, 1.0 mmol) was added to a stirred mixture of 3-(1-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperidin-4-yloxy)-benzoic acid methyl ester (prepared by the method used to generate Example 92) (99 mg, 0.2 mmol) in MeOH: H2O (1:1, 4 mL) was added, and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was concentrated under reduced pressure. Cold water was then added and acidified it with 10% aqueous HCl and extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure The residue was purified by washing with diethyl ether to afford 87 mg (97.7% Yield) 3-(1-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-piperidin-4-yloxy)-benzoic acid. LC/MS [M+H]+: 463, 96.9%. 1H NMR (300 MHz, DMSO-d6): δ13.8 (b, 1H), 13.6 (b, 1H), 8.1 (b, 1H), 7.8 (q, 2H), 7.5 (m, 6H), 7.3 (m, 1H), 7.1 (b, 1H), 4.8 (m, 1H), 4.2 (m, 2H), 3.9 (m, 1H), 3.8 (m, 1H), 3.4 (m, 2H), 2.0 (m, 2H), 1.7 (m, 1H).

Workup

  1. customprepared by the method
  2. additionwas added
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionCold water was then added
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure The residue
  8. customwas purified
  9. washby washing with diethyl ether

Sources & evidence

ORD record
ord-d0587f46f64e401fa669e2a0c5f994a5
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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