N-(3-Aminopropyl)morpholine → 3-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]-N-(3-morpholin-4-ylpropyl)benzamide

HRID 884653Notes

Reaction equation

HRID 884653 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]3[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=3)[C:18](O)=[O:19])[NH:11][C:12](=[O:14])[N:13]=2)=[CH:4][C:3]=1[CH3:24].[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][CH2:33][NH2:34])[CH2:27][CH2:26]1.ON1C2C=CC=CC=2N=N1.CCN=C=NCCC[N+](C)(C)C.[I-]>ClC(Cl)C.CN(C)C=O>[OH:19][C:18]1[CH:22]=[CH:23][C:15]([C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[C:7]([CH:24]=[CH:3][CH:4]=3)[C:2]([NH:34][CH2:33][CH2:32][CH2:31][N:28]3[CH2:29][CH2:30][O:25][CH2:26][CH2:27]3)=[O:1])[NH:13][C:12](=[O:14])[N:11]=2)=[CH:16][C:17]=1[CH3:21]

Participants

7

Reactant 4

HCID 61055N-(3-Aminopropyl)morpholineHCID 757711-HydroxybenzotriazoleHCID 1222421-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodideHCID 1784225943-(6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl)benzoic acid2×

Product 1

HCID 1784225923-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]-N-(3-morpholin-4-ylpropyl)benzamideYield 27.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

3-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]benzoic acid (Compound 289, 15.5 mg, 48 umol) and commercially available 3-morpholinopropan-1-amine (5.8 mg, 40 umol) were dissolved in dichloroethane (1.25 mL) and N,N-dimethylformamide (0.79 mL). To this solution was added commercially available 1-hydroxybenzotriazole (6.8 mg, 50 umol) followed by commercially available 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide (17.8 mg, 60 umol). The reaction mixture was stirred at room temperature for 15 hours and was concentrated in vacuo. The reaction mixture was purified by reverse phase HPLC to give 5 mg of product. 1H NMR (400 MHz, d6-DMSO): δ 8.65 (t, 1H), 8.51 (s, 1H), 8.28-8.23 (m, 2H), 8.02-7.96 (m, 2H), 7.87 (dd, 1H), 7.63 (t, 1H), 7.46 (s, 1H), 6.92 (d, 1H), 3.56 (t, 4H), 3.36-3.32 (m, 2H), 2.40-2.33 (m, 6H), 2.20 (s, 3H), 1.78-1.68 (m, 2H). MS (EI): 450 (MH+).

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe reaction mixture was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-54203982f81b428c82f66e02ef924424
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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