Hydrazine → HCID 86681365, compound

HRID 1406664Notes

Reaction equation

HRID 1406664 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]([O:21]CC)=O)[CH2:14][CH2:13]1.[NH2:24][NH2:25]>C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]([NH:24][NH2:25])=[O:21])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86681366HCID 86681366, compound

Product 1

HCID 86681365HCID 86681365, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{25} (5.74 g, 18.4 mmol, 1 equiv.), anhydrous hydrazine (1.7 mL, 55.2 mmol, 3 equiv.), ethanol (37.2 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{25} (4.49 g, 82%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 8.17 (br s, 1H), 7.82-7.78 (m, 3H), 7.71 (s, 1H), 7.47-7.42 (m, 3H), 3.86 (br s, 2H), 3.64 (s, 2H), 3.06 (s, 2H), 2.53 (br s, 8H). 13C-NMR (125 MHz, CDCl3): δ 170.4, 135.4, 133.1, 132.6, 127.8, 127.5, 127.5, 127.2, 125.9, 125.5, 62.9, 60.5, 53.5, 53.0.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{25} (4.49 g, 82%) as a white solid

Sources & evidence

ORD record
ord-8c0cea23890f47d59302059e44e90826
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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