Hydrazine → HCID 86681355, compound

HRID 1406647Notes

Reaction equation

HRID 1406647 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14](OCC)=[O:15])[CH2:9][CH2:8]1.[NH2:26][NH2:27]>C(O)C>[CH3:25][O:24][C:20]1[CH:19]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:21]=1[O:22][CH3:23])[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]([NH:26][NH2:27])=[O:15])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86681356HCID 86681356, compound

Product 1

HCID 86681355HCID 86681355, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{16} (5.99 g, 17.0 mmol, 1 equiv.), anhydrous hydrazine (1.6 mL, 51.0 mmol, 3 equiv.), ethanol (34.2 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{16} (4.93 g, 86%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 8.14 (br s, 1H), 6.47 (s, 2H), 3.83 (br s, 2H), 3.78 (s, 6H), 3.76 (s, 3H), 3.36 (s, 2H), 3.01 (s, 2H), 2.48 (br s, 4H), 2.39 (br s, 4H). 13C-NMR (125 MHz, CDCl3): δ 170.2, 152.8, 136.6, 133.6, 105.4, 62.8, 60.6, 60.4, 55.9, 53.4, 52.8.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{16} (4.93 g, 86%) as a white solid

Sources & evidence

ORD record
ord-75a86cb707c041daad2a80837d2619b8
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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