Hydrazine → HCID 86681353, compound

HRID 1406645Notes

Reaction equation

HRID 1406645 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([O:17]CC)=O)[CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[NH2:24][NH2:25]>C(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:24][NH2:25])=[O:17])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86681354HCID 86681354, compound

Product 1

HCID 86681353HCID 86681353, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{15} (4.76 g, 14.4 mmol, 1 equiv.), anhydrous hydrazine (1.4 mL, 43.2 mmol, 3 equiv.), ethanol (28.9 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{15} (3.70 g, 81%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 8.13 (br s, 1H), 7.55 (d, 2H, J=8.0 Hz), 7.41 (d, 2H, J=8.0 Hz), 3.84 (br s, 2H), 3.53 (s, 2H), 3.07 (s, 2H), 2.53 (br s, 4H), 2.45 (br s, 4H). 13C-NMR (125 MHz, CDCl3): δ 170.3, 142.2, 129.3 (q, JC-F=32.0 Hz), 129.0, 125.1 (q, JC-F=3.8 Hz), 19624.1 (q, JC-F=270.5 Hz) 129.1, 62.2, 60.5, 53.6, 53.0. 19F-NMR (470 MHz, CDCl3): δ-62.8.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{15} (3.70 g, 81%) as a white solid

Sources & evidence

ORD record
ord-6906f0a7597f484580a35765b4f468b7
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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