Hydrazine → HCID 66897731, compound

HRID 241616Notes

Reaction equation

HRID 241616 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[C:9]3[C:14]([C:15]=2[C:16](=[NH:18])[O-])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:26])[O:4][N:3]=1.[NH2:27][NH2:28]>CCO.CCOC(C)=O>[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)[C:9]3[C:14]([C:15]=2[C:16](=[N:27][NH2:28])[NH2:18])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:26])[O:4][N:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 178434748HCID 178434748, compound

Product 1

HCID 66897731HCID 66897731, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

2-(3,5-Dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indole-3-carbimidate (Example 184) was dissolved in EtOH and 10 eq hydrazine was added. The resulting mixture was stirred at 90° C. for 10 hours. The reaction mixture was diluted with EtOAc and washed with brine. The organic phase was evaporated to dryness in vacuo and then purified using reversed phase preparative HPLC. Fractions were combined, concentrated and the final product was identified by 1H-NMR and LC/MS. Purity was determined by analytical HPLC. ES/MS m/z: 362.21 (M+H), 360.28 (M−H); 1H NMR (methanol-d3, 500 MHz): 7.81 (m, 1H), 7.36-7.32 (m, 3H), 7.08 (m, 2H), 6.90 (m, 2H), 2.16 (s, 3H) and 1.96 (s, 3H).

Workup

  1. washwashed with brine
  2. customThe organic phase was evaporated to dryness in vacuo
  3. custompurified
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1082388e482d426ba0f1aab771d98c01
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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