Hydrazine → HCID 86707736, compound

HRID 1190844Notes

Reaction equation

HRID 1190844 reaction equation
[CH3:1][S:2]([CH:5]([C:11]1[S:12][C:13]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=[CH:16][C:14]=2[N:15]=1)C(OCC)=O)(=[O:4])=[O:3].NN>CCO>[CH3:1][S:2]([CH2:5][C:11]1[S:12][C:13]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=[CH:16][C:14]=2[N:15]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86707735HCID 86707735, compound

Product 1

HCID 86707736HCID 86707736, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Compound 89a (100 mg, 0.27 mmol) in EtOH (8 mL) was added hydrazine (0.13 mL, 4.0 mmol) and the reaction mixture stirred at rt for 1 h, then at 50° C. for 1 h. The reaction mixture was allowed to cool, concentrated under reduced pressure and the residue suspended in DCM, filtered and dried under vacuum to give Compound 89b (22 mg, 23% yield). RT=1.65 min using analytical method (Q), 361.9 (M+H). 1H NMR (500 MHz, DMSO-d6) δ 8.51-8.45 (m, 1H), 8.15 (d, J=8.5 Hz, 1H), 7.87 (dd, J=8.5, 1.9 Hz, 1H), 7.77 (d, J=7.4 Hz, 2H), 7.53-7.49 (m, 2H), 7.44-7.38 (m, 1H), 5.80 (s, 1H), 3.24 (s, 3H).

Workup

  1. waitat 50° C. for 1 h
  2. temperatureto cool
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-657a3f8b3f084793baed24947808b7e9
Source dataset
uspto-grants-2014_03
Patent number
US08680090B2

Reaction notes

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