1-Hydroxybenzotriazole → (E)-3-[5-methoxy-6-(4-methyl-1H-imidazol-1-yl)pyridin-3-yl]-N-(2-oxo-3-phenyl-tetrahydropyrimidin-1-yl)acrylamide

HRID 546752Notes

Reaction equation

HRID 546752 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]1=[O:14].C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:34][O:35][C:36]1[CH:37]=[C:38](/[CH:48]=[CH:49]/[C:50](O)=[O:51])[CH:39]=[N:40][C:41]=1[N:42]1[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]1>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH3:34][O:35][C:36]1[CH:37]=[C:38](/[CH:48]=[CH:49]/[C:50]([NH:1][N:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:3]2=[O:14])=[O:51])[CH:39]=[N:40][C:41]=1[N:42]1[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 668394721-Amino-3-phenyl-tetrahydropyrimidin-2-oneHCID 66839567(E)-3-[5-methoxy-6-(4-methyl-1H-imidazol-1-yl)pyridin-3-yl]acrylic acid

Product 1

HCID 66839535(E)-3-[5-methoxy-6-(4-methyl-1H-imidazol-1-yl)pyridin-3-yl]-N-(2-oxo-3-phenyl-tetrahydropyrimidin-1-yl)acrylamide

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Amino-3-phenyl-tetrahydropyrimidin-2-one synthesized by the same method as in Example 232 at room temperature (111 mg; ESI-MS; m/z 192 [M++H]), IPEA (0.41 mL), EDC (166 mg) and HOBT (117 mg) were added to a solution of (E)-3-[5-methoxy-6-(4-methyl-1H-imidazol-1-yl)pyridin-3-yl]acrylic acid (300 mg) in DMF (6 mL). The reaction solution was stirred at room temperature for 24 hours. The reaction solution was diluted with ethyl acetate and washed with a saturated sodium bicarbonate solution and a saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system, then ethyl acetate-methanol system) to obtain 250 mg of the title compound. The property value of the compound is as follows.

Workup

  1. washwashed with a saturated sodium bicarbonate solution
  2. dry with materialThe resulting organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (carrier
  5. washelution solvent

Sources & evidence

ORD record
ord-dc3242df9df74d0d86d85f721db5ee20
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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