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

HRID 1794598
Notes
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Reaction equation

HRID 1794598 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.Cl.[NH2:24][CH2:25][CH2:26][C:27]([NH2:29])=[O:28].CCN(C(C)C)C(C)C>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:24][CH2:25][CH2:26][C:27]([NH2:29])=[O:28])[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 222222883-Aminopropanamide hydrochlorideHCID 222223445-Benzyl-6-(1-bromo-propyl)-3-methyl-5h-isoxazolo[5,4-d]pyrimidin-4-one

Product 1

HCID 22222259(+/-)-3-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propylamino]-propionamideYield 49%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

A solution of the compound of Example 1 Step 4 (2.0 g, 5.5 mmol) in EtOH (50 mL) was treated with 3-amino-propionamide hydrochloride (1.72 g, 13.8 mmol) and DIEA (0.53 g, 27.7 mmol). The resulting mixture was stirred at reflux for 6 h, then cooled to room temperature and concentrated under vacuum. The crude product was dissolved in CH3OH and 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 (0.96 g, 49%); 1H NMR (CD3OD): δ 7.37 (m, 5H), 5.65 (d, J=16.5 Hz, 1H), 5.30 (d, J=16.5 Hz, 1H), 4.70 (t, J=6.0 Hz, 1H), 3.15 (m, 1H), 2.94 (m, 1H), 2.59 (s, 3H), 2.49 (m, 2H), 1.93 (m, 2H), 0.89 (t, J=7.5 Hz, 3H); LC/MS (ESI): 370 (M+H)+.

Workup

  1. temperatureat reflux for 6 h
  2. concentrationconcentrated under vacuum
  3. dissolutionThe crude product was dissolved in CH3OH
  4. custompurified by preparative reverse-phase HPLC (CH3OH/H2O) on a YMC S10 ODS 50×500 mm column

Sources & evidence

ORD record
ord-9dc63d89886b40f0ab1a45e4f1e2cb93
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07022850B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes