3-Aminopropionitrile → (+/-)-3-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propylamino]-propionitrile

HRID 1794597

Reaction equation

HRID 1794597 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][O:17][C:11]=2[N:10]=[C:9]1[CH:19](Br)[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:23][CH2:24][CH2:25][C:26]#[N:27]>CCO>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([CH3:18])=[N:16][O:17][C:11]=2[N:10]=[C:9]1[CH:19]([NH:27][CH2:26][CH2:25][C:24]#[N:23])[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 16473-AminopropionitrileHCID 222223445-Benzyl-6-(1-bromo-propyl)-3-methyl-5h-isoxazolo[5,4-d]pyrimidin-4-one

Product 1

HCID 22222326(+/-)-3-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propylamino]-propionitrileYield 62.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the compound of Example 1 Step 4 (2.0 g, 5.5 mmol) in EtOH (50 mL) treated 3-amino-propionitrile (1.55 g, 22.1 mmol) and stirred at reflux for 6 h. The mixture was cooled to room temperature and concentrated under vacuum. The resulting material was purified by preparative reverse-phase HPLC (CH3OH/H2O) on a YMC S10 ODS 50×500 mm column to afford the desired product as a yellow glass (1.2 g, 62%); 1H NMR (CD3OD): δ 7.38 (m, 5H), 5.65 (d, J=16.5 Hz, 1H), 5.30 (d, J=16.5 Hz, 1H), 4.65 (t, J=6.0 Hz, 1H), δ 3.15 (m, 1H), 2.72 (m, 1H), 2.70 (t, J=7.5 Hz, 2H), 2.59 (s, 3H), 1.92 (m, 2H), 0.89 (t, J=7.5 Hz, 3H)); LC/MS (ESI): 352 (M+H)+.

Workup

  1. temperatureat reflux for 6 h
  2. concentrationconcentrated under vacuum
  3. customThe resulting material was purified by preparative reverse-phase HPLC (CH3OH/H2O) on a YMC S10 ODS 50×500 mm column

Sources & evidence

ORD record
ord-b720e3ebc86343e980ab11239918d7e7
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Linked notes

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