Lithium Hydroxide → HCID 90404220, compound

HRID 924212Notes

Reaction equation

HRID 924212 reaction equation
[C:1](/[C:3](=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:20]=[CH:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=3)[N:17]=2)=[CH:12][CH:11]=1)/[C:4]([O:6]CC)=[O:5])#[N:2].[OH-].[Li+]>O1CCCC1.CO.O>[C:1](/[C:3](=[CH:9]/[C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:20]=[CH:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:23][CH:22]=3)[N:17]=2)=[CH:14][CH:15]=1)/[C:4]([OH:6])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90438206HCID 90438206, compound

Product 1

HCID 90404220HCID 90404220, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To (Z)-ethyl 2-cyano-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acrylate (C46) (2.5 g, 5.8 mmol) in tetrahydrofuran/methanol/water (3:2:1, 42 mL) was added lithium hydroxide (2.5 mL, 7.5 mmol) and stirred at room temperature for 18 hours. The reaction mixture was concentrated under vacuum, cooled in an ice bath, and acidified with hydrogen chloride (2 N). The precipitate was filtered and washed with cold water to afford the title compound as a brown solid (2.2 g, 82%): 1H NMR (400 MHz, DMSO-d6) δ 9.49 (s, 1H), 8.39 (s, 1H), 8.28 (d, J=8.5 Hz, 2H), 8.18 (d, J=8.5 Hz, 2H), 8.13-8.08 (m, 2H), 7.64 (d, J=8.4 Hz, 2H); ESIMS m/z 401 ([M+H]+).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. temperaturecooled in an ice bath
  3. filtrationThe precipitate was filtered
  4. washwashed with cold water

Sources & evidence

ORD record
ord-eeff5e768077441b90fd91be2a8fe9d0
Source dataset
uspto-grants-2016_03
Patent number
US09278964B2

Reaction notes

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