Hydrazine → HCID 90031283, compound

HRID 1771266Notes

Reaction equation

HRID 1771266 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16](OCC)=[O:17])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1)#[N:2].[NH2:23][NH2:24]>CCO>[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([NH:23][NH2:24])=[O:17])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 90031387HCID 90031387, compound

Product 1

HCID 90031283HCID 90031283, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C with modification as noted: 51e (5.59 g, 18.6 mmol, 1.0 equiv.), anhydrous hydrazine (2.4 mL, 74.4 mmol, 4.0 equiv.), EtOH (35 mL, 0.5 M). After extraction with CH2Cl2, the aqueous layer was extracted with EtOAc (3×). 46e (2.98 g, 55.8%) was obtained as an off-white solid after extraction without further purification. 1H-NMR (500 MHz, CDCl3) δ 8.02 (br s, 1H), 7.70 (d, 2H, J=8.5 Hz), 7.48 (d, 2H, J=8.5 Hz), 3.86 (br d, 2H, J=3.5 Hz), 3.78 (br s, 2H), 3.37 (br s, 2H), 3.11 (s, 2H), 2.60 (br s, 2H), 2.46 (br s, 2H). 13C-NMR (125 MHz, CDCl3) δ 169.8, 168.4, 139.8, 132.6, 127.9, 118.1, 113.8, 60.6, 53.8 (br), 53.3 (br), 47.6 (br), 42.2 (br). HRMS (ESI): 288.1464 (M+1); calcd. for C14H18N5O2: 288.1461.

Workup

  1. customSynthesized
  2. extractionAfter extraction with CH2Cl2
  3. extractionthe aqueous layer was extracted with EtOAc (3×)

Sources & evidence

ORD record
ord-49ab034d52934e3f87267a80729ee942
Source dataset
uspto-grants-2016_02
Patent number
US09249116B2

Reaction notes

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