Hydrazine → HCID 86681367, compound

HRID 1406666Notes

Reaction equation

HRID 1406666 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18]CC)=O)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[NH2:27][NH2:28]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]([NH:27][NH2:28])=[O:18])[CH2:13][CH2:14]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86681368HCID 86681368, compound

Product 1

HCID 86681367HCID 86681367, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{26} (7.25 g, 19.4 mmol, 1 equiv.), anhydrous hydrazine (1.8 mL, 58.3 mmol, 3 equiv.), ethanol (39.2 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{26} (6.54 g, 94%) as a yellow oil. 1H-NMR (500 MHz, CDCl3): δ 8.15 (br s, 1H), 7.35-7.32 (m, 4H), 7.27-7.22 (m, 4H) 7.19-7.16 (m, 1H), 4.20 (s, 1H), 3.84 (br s, 2H), 3.06 (s, 2H), 2.52 (br s, 4H), 2.38 (br s, 4H). 13C-NMR (125 MHz, CDCl3): δ 170.3, 141.7, 140.9, 132.5, 129.0, 128.5, 128.5, 127.6, 127.1, 75.1, 60.4, 53.7, 51.6.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{26} (6.54 g, 94%) as a yellow oil

Sources & evidence

ORD record
ord-402313f8495c4be2ba1ea647a3d32d10
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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