Hydrazine → HCID 86681357, compound

HRID 1406649Notes

Reaction equation

HRID 1406649 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:22]=[CH:21][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18]CC)=O)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.[NH2:25][NH2:26]>C(O)C>[F:1][C:2]([F:23])([F:24])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]([NH:25][NH2:26])=[O:18])[CH2:13][CH2:14]2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86681358HCID 86681358, compound

Product 1

HCID 86681357HCID 86681357, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{17} (5.57 g, 16.1 mmol, 1 equiv.), anhydrous hydrazine (1.5 mL, 48.3 mmol, 3 equiv.), ethanol (32.4 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{17} (4.67 g, 87%) as a beige solid. 1H-NMR (500 MHz, CDCl3): δ 8.15 (br s, 1H), 7.28 (d, 2H, J=8.0 Hz), 7.11 (d, 2H, J=8.0 Hz), 3.83 (br s, 2H), 3.45 (s, 2H), 3.03 (s, 2H), 2.49 (br s, 4H), 2.41 (br s, 4H). 13C-NMR (125 MHz, CDCl3): δ 170.3, 148.1, 136.7, 130.1, 120.5, 120.3 (q, JC-F=255.5 Hz), 61.8, 60.4, 53.5, 52.9. 19F-NMR (470 MHz, CDCl3): −58.3.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{17} (4.67 g, 87%) as a beige solid

Sources & evidence

ORD record
ord-e0d799e475654ca4ba92265ea80cc4c0
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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