Hydrazine → HCID 16637145, compound

HRID 1771264Notes

Reaction equation

HRID 1771264 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18]CC)=O)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:21][NH2:22]>CCO>[C:1]([N:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]([NH:21][NH2:22])=[O:18])[CH2:13][CH2:14]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 46673126HCID 46673126, compound

Product 1

HCID 16637145HCID 16637145, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 51c (2.87 g, 10.4 mmol, 1.0 equiv.), anhydrous hydrazine (1.31 mL, 41.6 mmol, 4.0 equiv.), EtOH (20 mL, 0.5 M). 46c (1.41 g, 51.5%) was obtained as a white solid after extraction without further purification. 1H-NMR (500 MHz, CDCl3) δ 8.10 (s, 1H), 7.39-7.34 (m, 5H), 3.84 (br s, 2H), 3.77 (br s, 2H), 3.43 (br s, 2H), 3.08 (s, 2H), 2.56 (br s, 2H), 2.44 (br s, 2H). 13C-NMR (125 MHz, CDCl3) δ 170.5, 169.9, 135.5, 130.0, 128.7, 127.1, 60.6, 53.9 (br), 53.4 (br), 47.7 (br), 42.2 (br). HRMS (ESI): 263.1513 (M+1); calcd. for C13H19N4O2: 263.1508.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-f71ed9fb06ab416aab908d1e457ec76c
Source dataset
uspto-grants-2016_02
Patent number
US09249116B2

Reaction notes

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