Hydrazine hydrate (1:1) → HCID 178506369, compound

HRID 2373343Notes

Reaction equation

HRID 2373343 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([NH2:15])=O.O.[NH2:22]N.COC(OC)[N:27]([CH3:29])C>C(O)(=O)C>[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[C:12]([C:13]2[N:27]=[CH:29][NH:22][N:15]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 59654362HCID 59654362, compound

Product 1

HCID 178506369HCID 178506369, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 0.137 g (0.48 mmol) of 3-(2-trifluoromethoxyphenyl)-benzamide in 1 mL of N,N-dimethylformamide dimethyl acetal was heated at 120° C. for 2 h at which time the reaction was concentrated in vacuo. To this material in 2.3 mL of acetic acid was added 0.028 g (0.55 mmol) of hydrazine hydrate and the reaction mixture was heated at 90° C. for 2 h. The reaction mixture was then concentrated and partitioned between EtOAc and saturated NaHCO3 solution. The organic fraction was washed with brine, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, 30:1, 9:1, 3:1 successively CH2Cl2: acetone) to give the title compound. 1H NMR (CD3OD) (δ, ppm): 8.32 (s, 1H), 8.06 (s, 1H), 7.98 (m, 1H), 7.50 (m, 3H), 7.39(m, 3H). Mass Spectrum (ESI) m/e (M+1): 306.1.

Workup

  1. concentrationwas concentrated in vacuo
  2. concentrationThe reaction mixture was then concentrated
  3. custompartitioned between EtOAc and saturated NaHCO3 solution
  4. washThe organic fraction was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chromatography (silica, 30:1, 9:1, 3:1 successively CH2Cl2

Sources & evidence

ORD record
ord-dcd35586fa5f450582e86994830366a0
Source dataset
uspto-grants-2008_12
Patent number
US07459475B2

Reaction notes

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