Hydrazine → HCID 86681359, compound

HRID 1406656Notes

Reaction equation

HRID 1406656 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23](OCC)=[O:24])[CH2:18][CH2:17]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[NH2:28][NH2:29]>C(O)C>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]([NH:28][NH2:29])=[O:24])[CH2:18][CH2:17]2)=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86681360HCID 86681360, compound

Product 1

HCID 86681359HCID 86681359, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{21} (6.82 g, 18.8 mmol, 1 equiv.), anhydrous hydrazine (1.8 mL, 56.4 mmol, 3 equiv.), ethanol (38.0 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{21} (3.56 g, 54%) as an orange semi-solid. 1H-NMR (500 MHz, CDCl3): δ 8.46 (d, 2H, J=8.5 Hz), 8.42 (s, 1H), 8.21 (br s, 1H), 8.01 (d, 2H, J=8.5 Hz), 7.53 (ddd, 2H, J=1.5, 6.5, 8.0 Hz), 7.47 (ddd, 2H, J=1.0, 6.5, 8.0 Hz), 4.45 (s, 2H), 3.87 (br s, 2H), 3.04 (s, 2H), 2.64 (br s, 4H), 2.47 (br s, 4H). 13C-NMR (125 MHz, CDCl3): δ 170.5, 131.3, 131.3, 129.2, 128.9, 127.5, 125.6, 124.9, 124.8, 60.4, 54.0, 53.7, 53.1.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{21} (3.56 g, 54%) as an orange semi-solid

Sources & evidence

ORD record
ord-f89201ed8bce4b83a34633d29876bdfa
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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