Hydrazine hydrate (1:1) → HCID 90410960, compound

HRID 525286Notes

Reaction equation

HRID 525286 reaction equation
[CH:1]12[CH2:7][CH:5]([O:6]1)[CH2:4][N:3]([C:8]1[CH:17]=[C:16]3[C:11]([N:12]=[CH:13][CH:14]=[N:15]3)=[C:10]([O:18][CH:19]3[CH2:24][CH2:23][CH:22]([N:25]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:21][CH2:20]3)[CH:9]=1)[CH2:2]2.O.NN>CCO>[CH:5]12[CH2:7][CH:1]([O:6]1)[CH2:2][N:3]([C:8]1[CH:17]=[C:16]3[C:11]([N:12]=[CH:13][CH:14]=[N:15]3)=[C:10]([O:18][CH:19]3[CH2:20][CH2:21][CH:22]([NH2:25])[CH2:23][CH2:24]3)[CH:9]=1)[CH2:4]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 90413122HCID 90413122, compound

Product 1

HCID 90410960HCID 90410960, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-[4-[7-(6-oxa-3-azabicyclo[3.1.1]heptan-3-yl)quinoxalin-5-yl]oxycyclohexyl]isoindoline-1,3-dione (800 mg, 1.700 mmol) in EtOH (10 mL) was added hydrazine monohydrate (85.10 mg, 83.35 μL, 1.700 mmol) and the reaction was stirred at reflux overnight, then concentrated, diluted with DCM, and filtered. The filtrate was concentrated, and purified on a 40 g silica gel cartridge with 0-50% (20% NH3/MeOH) to yield 4-[7-(6-oxa-3-azabicyclo[3.1.1]heptan-3-yl)quinoxalin-5-yl]oxycyclohexanamine (450 mg, 77.8%) as a yellow solid. 1H NMR (300 MHz, Chloroform-d) ∂ 8.65 (d, J=1.9 Hz, 1H), 8.53 (d, J=1.9 Hz, 1H), 6.83 (q, J=2.6 Hz, 2H), 4.83 (t, J=6.0 Hz, 4H), 3.87-3.60 (m, 5H), 3.34 (dt, J=8.7, 6.6 Hz, 1H), 3.01-2.83 (m, 1H), 2.23 (dq, J=11.3, 5.8, 4.8 Hz, 2H), 2.07 (d, J=8.7 Hz, 1H), 1.92-1.62 (m, 6H).

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated
  3. additiondiluted with DCM
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified on a 40 g silica gel cartridge with 0-50% (20% NH3/MeOH)

Sources & evidence

ORD record
ord-b19cf06fd94a42bc8107236fa80e0b30
Source dataset
uspto-grants-2016_05
Patent number
US09340557B2

Reaction notes

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