Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1) → HCID 60142048, compound

HRID 1805278Notes

Reaction equation

HRID 1805278 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([C:18]([CH:23]=O)=[CH:19]N(C)C)[O:11][N:10]=1.Cl.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][NH2:34]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([C:18]2[CH:19]=[N:34][N:33]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[F:26])[CH:23]=2)[O:11][N:10]=1

Participants

4

Reactant 2

HCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)HCID 86668521HCID 86668521, compound

Product 1

HCID 60142048HCID 60142048, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
57.5 °C

Procedure

To a solution of raw methyl 3-(2-chloro-6-fluorophenyl)-5-[2-(dimethylamino)-1-formylvinyl]isoxazole-4-carboxylate (36 mg, 0.102 mmol) in ethanol (460 mg), 2-fluorophenyl hydrazine hydrochloride (16 mg, 0.100 mmol) was added. The mixture was warmed to 55-60° C. until a TLC sample showed no starting enamine. The solution was evaporated to dryness in vacuum, the reside was extracted with 3×10 ml of boiling hexane, and the hexane extracts were combined and concentrated and cooled to room temperature. Crystallization gave 25 mg of desired product (example I-89) (yield 60%). Result of LC/MS MH+: 416.05; 1H NMR (CDCl3): 3.67 (s, 3H), 7.30 (t, 1H), 7.45 (m, 4H), 7.57 (m, 1H), 7.93 (t, 1H), 8.50 (s, 1H), 9.13 (s, 1H).

Workup

  1. customThe solution was evaporated to dryness in vacuum
  2. extractionthe reside was extracted with 3×10 ml of boiling hexane
  3. concentrationconcentrated
  4. temperaturecooled to room temperature
  5. customCrystallization

Sources & evidence

ORD record
ord-558ea1b90bbb435db4418675e836f8f5
Source dataset
uspto-grants-2013_01
Patent number
US08354436B2

Reaction notes

Loading…