Lithium hydroxide, monohydrate → HCID 67252390, compound

HRID 1711667Notes

Reaction equation

HRID 1711667 reaction equation
O[Li].O.[C:4]([C:8]1[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[N:10]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[C:23]([NH:28][CH3:29])[CH:22]=[CH:21]3)[N:9]=1)([CH3:7])([CH3:6])[CH3:5]>O.C1COCC1.CCO.Cl>[C:4]([C:8]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[C:23]([NH:28][CH3:29])[CH:22]=[CH:21]3)[N:9]=1)([CH3:7])([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58851604HCID 58851604, compound

Product 1

HCID 67252390HCID 67252390, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

LiOH.H2O (0.143 g, 3.40 mmol) was added to a solution of ethyl 3-tert-butyl-1-(2-(methylamino)quinolin-6-yl)-1H-pyrazole-5-carboxylate (0.240 g, 0.68 mmol) in a mixture of water/THF/EtOH (1:1:1, 9 mL). The reaction mixture was stirred overnight at RT, diluted with 3 M HCl and extracted with EtOAc and THF. The combined organics were washed with brine, dried (MgSO4) and concentrated under vacuum to obtain 3-tert-butyl-1-(2-(methylamino)quinolin-6-yl)-1H-pyrazole-5-carboxylic acid (0.22 g, 100% yield). 1H-NMR (DMSO-d6) δ 7.90 (d, J=9.2 Hz, 1H), 7.66 (d, J=2.4 Hz, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.46 (dd, J=9.2, 2.8 Hz, 1H), 7.14 (m, 1H), 6.88 (brs, 1H), 6.79 (d, J=9.2 Hz, 1H), 2.92 (d, J=4.8 Hz, 3H), 1.31 (s, 9H); MS (ESI) m/z: 325.2 (M+H+).

Workup

  1. extractionextracted with EtOAc and THF
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-de85751e81c743a49897f2ec07da2d36
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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