1,1-Dichloroethane → 2-({4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)-N-(2-piperidin-1-ylethyl)acetamide

HRID 884659Notes

Reaction equation

HRID 884659 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]3[CH:20]=CC(OCC(O)=O)=[CH:17][CH:16]=3)[NH:11][C:12](=[O:14])[N:13]=2)=[CH:4][C:3]=1[CH3:26].[O:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][NH2:35])[CH2:29][CH2:28]1.[OH:36]N1C2C=CC=CC=2N=N1.CCN=C=N[CH2:51][CH2:52][CH2:53][N+](C)(C)C.[I-].Cl[CH:60](Cl)[CH3:61]>CN(C)C=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:15]3[CH:16]=[CH:17][C:32]([O:27][CH2:28][C:29]([NH:30][CH2:33][CH2:34][N:35]4[CH2:51][CH2:52][CH2:53][CH2:61][CH2:60]4)=[O:36])=[CH:31][CH:20]=3)[NH:11][C:12](=[O:14])[N:13]=2)=[CH:4][C:3]=1[CH3:26]

Participants

7

Reactant 5

HCID 63651,1-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 1222421-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodideHCID 4082852-MorpholinoethylamineHCID 136052111({4-[6-(4-Hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)acetic acid2×

Product 1

HCID 1360520702-({4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)-N-(2-piperidin-1-ylethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

({4-[6-(4-hydroxy-3-methylphenyl)-2-oxo-2,3-dihydropyrimidin-4-yl]phenyl}oxy)-acetic acid (Compound 266, 17 mg, 48 umol) and 2-morpholinoethanamine (5.2 mg, 40 umol) were dissolved in dichloroethane (1.25 mL) and N,N-dimethylformamide (0.79 mL). To this solution was added 1-hydroxybenzotriazole (6.8 mg, 50 umol) followed by 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 8.23 (s, 1H), 8.14 (d, 2H), 8.03 (t, 1H), 7.94 (s, 1H), 7.85 (d, 1H), 7.33 (s, 1H), 7.09 (dd, 2H), 6.90 (d, 1H), 4.59 (s, 2H), 3.27-3.24 (m, 2H), 2.37-2.33 (m, 6H), 2.20 (s, 3H), 1.49-1.44 (m, 4H), 1.38-1.34 (m, 2H). MS (EI): 464 (MH+).

Workup

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

Sources & evidence

ORD record
ord-366d905effc44422a234943e3b80a819
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

Loading…