Hydrazine → HCID 90033596, compound

HRID 1771265Notes

Reaction equation

HRID 1771265 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15](OCC)=[O:16])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].[NH2:22][NH2:23]>CCO>[C:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:22][NH2:23])=[O:16])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 90031854HCID 90031854, compound

Product 1

HCID 90033596HCID 90033596, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 51d (2.71 g, 9.43 mmol, 1.0 equiv.), anhydrous hydrazine (1.18 mL, 37.7 mmol, 4.0 equiv.), EtOH (19 mL, 0.5 M). 46d (1.73 g, 67.1%) was obtained as an off-white solid after extraction without further purification. 1H-NMR (500 MHz, CDCl3) δ 8.10 (br s, 1H), 7.60 (d, 2H, J=8.0 Hz), 7.43 (d, 2H, J=8.5 Hz), 3.84 (br d, 2H, J=5.0 Hz), 3.55 (s, 2H), 3.08 (s, 2H), 2.55 (br s, 4H), 2.46 (br s, 4H). 13C-NMR (125 MHz, CDCl3) δ 170.6, 144.1, 132.4, 129.6, 119.1, 111.2, 62.5, 60.8, 53.8, 53.3. HRMS (ESI): 274.1673 (M+1); calcd. for C14H20N5O: 274.1668.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-19fc139db146492891f88387f1281b5b
Source dataset
uspto-grants-2016_02
Patent number
US09249116B2

Reaction notes

Loading…