Hydrazine hydrate (1:1) → HCID 57435096, compound

HRID 1366913Notes

Reaction equation

HRID 1366913 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([O:6][C:7](=[O:22])[C:8](=O)[CH2:9][C:10](=O)[CH2:11][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:13])[CH3:5]>CCO>[CH2:4]([O:6][C:7]([C:8]1[CH:9]=[C:10]([CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[NH:3][N:2]=1)=[O:22])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57435095HCID 57435095, compound

Product 1

HCID 57435096HCID 57435096, compoundYield 6.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.134 mL, 2.76 mmol) was added to a stirring room temperature solution of 56 0.7230 g, 2.76 mmol) in EtOH (2.8 mL, 1 M) under N2. The reaction was then heated to reflux until judged complete by HPLC (50 min): The reaction was concentrated and purified by preparative reverse phase HPLC with the following conditions: 0 to 24 min, 55:45 H2O:CH3CN; 24-25 min, 55:45 to 0:100H2O:CH3CN; 20 mL/min.; λ=214 nM; 100 mg/mL, 0.2 mL/injection. 0.0489 g of 57 was obtained. 1H (CDCl3, 300 MHz): δ 10.77 (1H, broad s), 7.36-7.14 (5H, m), 6.49 (1H, s), 4.33 (2H, q, J=7.0 Hz), 3.16-2.86 (3H, m), 1.33 (3H, t, J=7.0 Hz), 1.27 (3H, d, J=5.9 Hz) ppm. 13C (CDCl3, 75 MHz): δ 162.01, 145.94, 145.75, 141.50, 128.43, 126.76, 126.32, 106.98, 60.87, 39.94, 34.64, 21.34, 14.12 ppm. DEPT (CDCl3, 75 MHz): CH3 carbons: 21.34, 14.12; CH2 carbons: 60.87, 34.64; CH carbons: 128.43, 126.77, 126.32, 106.98, 39.94 ppm. HPLC: 10.052 min.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux
  3. customuntil judged complete by HPLC (50 min)
  4. concentrationThe reaction was concentrated
  5. custompurified by preparative reverse phase HPLC with the following conditions
  6. custom0 to 24 min, 55:45 H2O
  7. custom24-25 min, 55:45

Sources & evidence

ORD record
ord-17f0cb01145245dd806e87650047ff9a
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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