Hydrazine → HCID 86681364, compound

HRID 1406662Notes

Reaction equation

HRID 1406662 reaction equation
[C:1]1([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([O:21]CC)=O)[CH2:14][CH2:13]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[NH2:24][NH2:25]>C(O)C>[C:1]1([CH2:11][N:12]2[CH2:13][CH2:14][N:15]([CH2:18][C:19]([NH:24][NH2:25])=[O:21])[CH2:16][CH2:17]2)[C:2]2[C:7](=[CH:8][CH:9]=[CH:4][CH:3]=2)[CH:6]=[CH:5][CH:10]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 6465878HCID 6465878, compound

Product 1

HCID 86681364HCID 86681364, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{24} (8.29 g, 26.5 mmol, 1 equiv.), anhydrous hydrazine (2.5 mL, 79.6 mmol, 3 equiv.), ethanol (53.4 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{24} (6.86 g, 87%) as a brown oil. 1H-NMR (500 MHz, CDCl3): δ 8.70 (d, 1H, J=8.0 Hz), 8.19 (br s, 1H), 7.84 (d, 1H, J=7.5 Hz), 7.77 (dd, 1H, J=3.0, 6.5 Hz), 7.52-7.46 (m, 2H), 7.41-7.38 (m, 2H), 3.90 (s, 2H), 3.87 (br s, 2H), 3.06 (s, 2H), 2.51 (br s, 8H). 13C-NMR (125 MHz, CDCl3): δ 170.5, 133.7, 133.7 132.4, 128.3, 127.9, 127.3, 125.6, 125.5, 125.0, 124.6, 60.9, 60.5, 53.6, 53.2.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{24} (6.86 g, 87%) as a brown oil

Sources & evidence

ORD record
ord-3aaf2a6e56ce4a44b8ed6f32b42e080f
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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