Hydrazine → HCID 89499464, compound

HRID 1771263Notes

Reaction equation

HRID 1771263 reaction equation
[C:1]([C:5]1[CH:23]=[CH:22][C:8]([CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]([O:19]CC)=O)[CH2:12][CH2:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:24][NH2:25]>C(O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]([NH:24][NH2:25])=[O:19])[CH2:14][CH2:15]2)=[CH:22][CH:23]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 89499366HCID 89499366, compound

Product 1

HCID 89499464HCID 89499464, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{20} (4.12 g, 12.9 mmol, 1 equiv.), anhydrous hydrazine (1.2 mL, 38.8 mmol, 3 equiv.), ethanol (26.0 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{20} (3.36 g, 84%) as a beige solid. 1H-NMR (500 MHz, CDCl3): δ 8.17 (br s, 1H), 7.31 (d, 2H, J=8.5 Hz), 7.20 (d, 2H, J=8.5 Hz), 3.85 (br s, 2H), 3.46 (s, 2H), 3.05 (s, 2H), 2.52 (br s, 4H), 2.45 (br s, 4H), 1.30 (s, 9H). 13C-NMR (125 MHz, CDCl3): δ 170.4, 149.9, 134.5, 128.7, 125.0, 62.4, 60.5, 53.5, 52.9, 34.3, 31.3.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{20} (3.36 g, 84%) as a beige solid

Sources & evidence

ORD record
ord-9d6a7bd4f94445938a152c126e524f04
Source dataset
uspto-grants-2016_02
Patent number
US09249116B2

Reaction notes

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