Hydrochloric Acid → HCID 59363796, compound

HRID 2189170Notes

Reaction equation

HRID 2189170 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH:22]([CH3:24])[CH3:23])=O)=[CH:6][C:3]=1[C:4]#[N:5].N1([CH2:34][C:35]([NH2:37])=[O:36])C2C=CC=CC=2N=N1.[OH-].[Na+].Cl>CCO>[F:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH:22]([CH3:24])[CH3:23])[NH:37][C:35](=[O:36])[CH:34]=2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23081252-BENZOTRIAZOL-1-YL-ACETAMIDEHCID 59363799HCID 59363799, compound

Product 1

HCID 59363796HCID 59363796, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (E)-2-fluoro-5-(3-(2-isobutoxyphenyl)-3-oxoprop-1-enyl)benzonitrile (324 mg, 1 mmol), commercially available 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetamide (176 mg, 1 mmol), and NaOH (80 mg) in 5 mL of EtOH was heated to 50° C. for 5 h. The reaction mixture was acidified with conc. HCl, concentrated and purified by preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate) to afford 2-fluoro-5-(6-{2-[(2-methylpropyl)oxy]phenyl}-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile (70 mg, 39%). 1H NMR (400 MHz, CDCl3): δ 7.90-7.80 (m, 2H), 7.78 (d, 1H), 7.46-7.33 (m, 2H), 7.13-7.03 (m, 2H), 6.62 (d, 2H), 3.85 (d, 2H), 2.21-2.14 (m, 1H), 1.06 (d, 6H). MS (EI) for C22H19FN2O2: 363 (MH+).

Workup

  1. concentrationconcentrated
  2. custompurified by preparative HPLC (reverse-phase, acetonitrile/water with 0.01% ammonium acetate)

Sources & evidence

ORD record
ord-cdf5703e74a645da83c934371298ef9b
Source dataset
uspto-grants-2012_12
Patent number
US08324231B2

Reaction notes

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