Diethyl Ether → HCID 178511707, compound

HRID 2200780Notes

Reaction equation

HRID 2200780 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[C:15]3[C:10]([N:11]=[CH:12][CH:13]=[N:14]3)=[C:9]([O:17][C@@H:18]3[CH2:23][CH2:22][C@H:21]([N:24]4C(=O)C5C(=CC=CC=5)C4=O)[CH2:20][CH2:19]3)[CH:8]=2)[CH2:3][CH2:2]1.NN.CCOCC>CO>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[C:15]3[C:10]([N:11]=[CH:12][CH:13]=[N:14]3)=[C:9]([O:17][C@@H:18]3[CH2:23][CH2:22][C@H:21]([NH2:24])[CH2:20][CH2:19]3)[CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9321HydrazineHCID 178515015HCID 178515015, compound

Product 1

HCID 178511707HCID 178511707, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As shown in step 9-iii of Scheme 9, to a suspension of 2-[(cis)-4-(7-morpholinoquinoxalin-5-yl)oxycyclohexyl]isoindoline-1,3-dione (2.3 g, 5.02 mmol) in MeOH (25 mL) was added hydrazine (321 mg, 315 μL, 10.0 mmol) and the reaction mixture stirred for 18 hours at RT, over which time the initial suspension became homogenenous followed by the appearance of a precipitate. Et2O (30 mL) was added and the reaction mixture stirred an additional 30 minutes. The precipitates were filtered off, the filtrate concentrated under reduced pressure, the residue treated with DCM (30 mL), and any remaining solids removed by filtration. The filtrate was concentrated under reduced pressure to provide (cis)-4-((7-morpholinoquinoxalin-5-yl)oxy)cyclohexanamine (compound 1030), which was used as is in subsequent reactions: 1H-NMR (300 MHz, CDCl3) δ 8.69 (d, J=1.9 Hz, 1H), 8.62 (d, J=1.9 Hz, 1H), 6.95 (d, J=2.5 Hz, 1H), 6.90 (d, J=2.5 Hz, 1H), 5.00-4.67 (m, 3H), 4.03-3.81 (m, 4H), 3.49 (s, 1H), 3.43-3.25 (m, 4H), 2.88 (q, J=6.2 Hz, 2H), 2.36-1.96 (m, 6H).

Workup

  1. filtrationThe precipitates were filtered off
  2. concentrationthe filtrate concentrated under reduced pressure
  3. additionthe residue treated with DCM (30 mL)
  4. customany remaining solids removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-42290441dfae4e3e8edd3c8429cb9bcb
Source dataset
uspto-grants-2016_06
Patent number
US09359380B2

Reaction notes

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