Hydrazine → HCID 86681369, compound

HRID 1406668Notes

Reaction equation

HRID 1406668 reaction equation
[I:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12](OCC)=[O:13])[CH2:7][CH2:6]1.[NH2:21][NH2:22]>C(O)C>[I:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]([NH:21][NH2:22])=[O:13])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86681370HCID 86681370, compound

Product 1

HCID 86681369HCID 86681369, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{27} (4.87 g, 12.5 mmol, 1 equiv.), anhydrous hydrazine (1.2 mL, 37.6 mmol, 3 equiv.), ethanol (25.0 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{27} (4.08 g, 87%) as a light yellow solid. 1H-NMR (400 MHz, CDCl3): δ 8.17 (br s, 1H), 7.82 (dd, 1H, J=1.2, 7.6 Hz), 7.37 (dd, 1H, J=1.6, 7.6 Hz), 7.29 (dt, 1H, J=1.2, 7.2), 6.91 (dt, 1H, J=1.6, 7.6 Hz), 3.85 (br s, 2H), 3.52 (s, 2H), 3.08 (s, 2H), 2.54 (br s, 8H). 13C-NMR (125 MHz, CDCl3): δ 170.5, 140.2, 139.5, 130.2, 128.7, 128.0, 100.6, 61.2, 60.6, 53.7, 52.9.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{27} (4.08 g, 87%) as a light yellow solid

Sources & evidence

ORD record
ord-c431b3d8ac0f4d728e1999d8567b01ff
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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