Hydrazine hydrate (1:1) → HCID 66752196, compound

HRID 522623Notes

Reaction equation

HRID 522623 reaction equation
[OH:1][C:2]([C:9]1[S:10][CH:11]=[C:12]([CH3:14])[N:13]=1)([CH3:8])[C:3](OCC)=[O:4].O.[NH2:16][NH2:17]>CCO>[OH:1][C:2]([C:9]1[S:10][CH:11]=[C:12]([CH3:14])[N:13]=1)([CH3:8])[C:3]([NH:16][NH2:17])=[O:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66751837HCID 66751837, compound

Product 1

HCID 66752196HCID 66752196, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Intermediate 106 (4.14 g, 19.23 mmol) in EtOH (60 mL) was treated with hydrazine monohydrate (FLUKA, 9.35 mL, 192 mmol). Mixture was heated at reflux for 3 h. Reaction mixture was concentrated. Residue was triturated with a mixture of DCM/Hexane and finally ether, and was filtered. Crude was purified by silica gel chromatography using a linear gradient of DCM/MeOH (0-5%) as eluents to obtain the title compound (3 g, 14.91 mmol, 78% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.05 (br s, 1H), 7.16 (s, 1H), 6.59 (s, 1H), 4.23-4.25 (m, 2H), 2.32 (s, 3H), 1.67 (s, 3H). [ES+MS] m/z 202 (MH+).

Workup

  1. temperatureMixture was heated
  2. temperatureat reflux for 3 h
  3. customReaction mixture
  4. concentrationwas concentrated
  5. customResidue was triturated with a mixture of DCM/Hexane and finally ether
  6. filtrationwas filtered
  7. customCrude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a0ece78181da4cf0af887b301ef38865
Source dataset
uspto-grants-2016_05
Patent number
US09334265B2

Reaction notes

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