Hydrazine → HCID 90001101, compound

HRID 1508307Notes

Reaction equation

HRID 1508307 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([C:24]1[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=1)=[CH:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12]1([CH2:18][N:17]([C:19](=[O:23])[CH:20](C)[CH3:21])[CH2:16]1)[O:11][CH2:10]2)=O.[NH2:35][NH2:36]>C(O)C.C(OCC)(=O)C>[Cl:32][C:26]1[CH:25]=[C:24]([C:3]2([C:2]([F:34])([F:33])[F:1])[NH:36][N:35]=[C:5]([C:7]3[CH:8]=[C:9]4[C:13](=[CH:14][CH:15]=3)[C:12]3([CH2:18][N:17]([C:19](=[O:23])[CH2:20][CH3:21])[CH2:16]3)[O:11][CH2:10]4)[CH2:4]2)[CH:29]=[C:28]([Cl:30])[C:27]=1[Cl:31]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 123850736HCID 123850736, compound

Product 1

HCID 90001101HCID 90001101, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the stirred solution of 4,4,4-trifluoro-1-(1-isobutyryl-3′H-spiro[azetidine-3,1′-isobenzofuran]-5′-yl)-3-(3,4,5-trichlorophenyl)but-2-en-1-one (Preparation 27, 0.5 g, 0.938 mmol, 1 eq) in ethanol (5 mL) was added hydrazine (1.0M solution in THF, 1.40 mL, 1.41 mmol, 1.5 eq). Resulting reaction mixture was refluxed for 2 hours under nitrogen atmosphere. After consumption of starting material, Reaction mixture was concentrated to get crude compound. Crude compound was dissolved in minimum quantity of ethyl acetate and adsorbed on silica gel (100-200 mesh). Crude compound purified by Combiflash chromatography using 40 g Redisep column. Desired compound was eluted in 55% ethyl acetate in hexane to afford title compound as off white solid (0.16 g, 31%). 1H NMR (400 MHz, DMSO-d6) δ: 1.00-1.06 (m, 6H), 2.53-2.56 (m, 1H), 3.75-3.88 (m, 2H), 4.10 (s, 2H), 4.40-4.45 (m, 2H), 5.08 (s, 2H), 7.57-7.58 (m, 2H), 7.66 (d, J=8.44 Hz, 1H), 7.88 (s, 2H), 8.91 (s, 1H). LC-MS (m/z): 546.0 (M+H). HPLC Purity: 96.43%.

Workup

  1. customResulting
  2. customreaction mixture
  3. temperaturewas refluxed for 2 hours under nitrogen atmosphere
  4. customAfter consumption of starting material, Reaction mixture
  5. concentrationwas concentrated
  6. customto get crude compound
  7. customCrude compound purified by Combiflash chromatography
  8. washDesired compound was eluted in 55% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ea271cbd323844d58a891698c018bf31
Source dataset
uspto-grants-2015_12
Patent number
US09221835B2

Reaction notes

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