Ethanol → HCID 57861273, compound

HRID 1960005Notes

Reaction equation

HRID 1960005 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-ef457ad93d5d42f383e9359439a3251c
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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