Hydrazine → HCID 86681361, compound

HRID 1406658Notes

Reaction equation

HRID 1406658 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:23]=1)[CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16](OCC)=[O:17])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[NH2:28][NH2:29]>C(O)C>[C:24]([C:22]1[CH:21]=[C:7]([CH:6]=[C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])[CH:23]=1)[CH2:8][N:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]([NH:28][NH2:29])=[O:17])[CH2:13][CH2:14]1)([CH3:26])([CH3:27])[CH3:25]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86681362HCID 86681362, compound

Product 1

HCID 86681361HCID 86681361, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 6{22} (4.57 g, 12.2 mmol, 1 equiv.), anhydrous hydrazine (1.1 mL, 36.6 mmol, 3 equiv.), ethanol (24.7 mL). Purification by silica gel column chromatography (4:1 EtOAc:MeOH) afforded 1{22} (2.88 g, 66%) as a beige solid. 1H-NMR (500 MHz, CDCl3): δ 8.17 (br s, 1H), 7.31 (t, 1H, J=1.5 Hz), 7.13 (d, 2H, J=1.5 Hz), 3.84 (br s, 2H), 3.51 (s, 2H), 3.08 (s, 2H), 2.55 (br s, 4H), 2.47 (br s, 4H), 1.32 (s, 18H). 13C-NMR (125 MHz, CDCl3): δ 170.5, 150.5, 136.7, 123.2, 120.9, 63.3, 60.6, 53.7, 52.9, 34.7, 31.5.

Workup

  1. customSynthesized
  2. customPurification by silica gel column chromatography (4:1 EtOAc:MeOH)
  3. customafforded 1{22} (2.88 g, 66%) as a beige solid

Sources & evidence

ORD record
ord-7f36b68cd41748db92995d4212c59120
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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