Ethanol → HCID 57861273, compound

HRID 1518049Notes

Reaction equation

HRID 1518049 reaction equation
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:6][N:7]([CH2:14][C:15]1[C:16]([N:27]([CH2:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:28][CH3:29])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=C(C#N)[CH:19]=2)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[Li+].[OH-:46].[CH3:47][CH2:48][OH:49]>Cl.C(OCC)(=O)C>[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:6][N:7]([CH2:14][C:15]1[C:16]([N:27]([CH2:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:28][CH3:29])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[C:47]([C:48]([OH:46])=[O:49])[CH:19]=2)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 57861269HCID 57861269, compound

Product 1

HCID 57861273HCID 57861273, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3-({N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amino}methyl)-2-[N′-(cyclopentylmethyl)-N′-ethylamino]quinoline-7-carbonitrile (40 mg, 0.06 mmol) and 2N LiOH aq. (2.0 mL) in EtOH (2 mL) is stirred and refluxed for 2 hours. The reaction mixture is cooled to room temperature and then diluted with 1N HCl and ethyl acetate. The organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated to give 3-({N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amino}methyl)-2-[N′-(cyclopentylmethyl)-N′-ethylamino]quinoline-7-carboxylic acid.

Workup

  1. temperaturerefluxed for 2 hours
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-94bc245356fa4263ab0d42cbf2acaa77
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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