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

HRID 546751Notes

Reaction equation

HRID 546751 reaction equation
C(N(C(C)C)CC)(C)C.[NH2:10][N:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:12]1=[O:24].C1C=CC2N(O)N=NC=2C=1.[CH3:35][O:36][C:37]1[N:42]=[C:41](/[CH:43]=[CH:44]/[C:45](O)=[O:46])[CH:40]=[CH:39][C:38]=1[N:48]1[CH:52]=[C:51]([CH3:53])[N:50]=[CH:49]1>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([N:13]2[CH2:14][CH2:15][CH2:16][N:11]([NH:10][C:45](=[O:46])/[CH:44]=[CH:43]/[C:41]3[CH:40]=[CH:39][C:38]([N:48]4[CH:52]=[C:51]([CH3:53])[N:50]=[CH:49]4)=[C:37]([O:36][CH3:35])[N:42]=3)[C:12]2=[O:24])=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66633906(E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylic acidHCID 668394801-Amino-3-(4-chlorophenyl)tetrahydropyrimidin-2-one

Product 1

HCID 66839690(E)-N-[3-(4-chlorophenyl)-2-oxo-tetrahydropyrimidin-1-yl]-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamideYield 99.8%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (0.65 mL), 1-amino-3-(4-chlorophenyl)tetrahydropyrimidin-2-one (139 mg), EDC (177 mg) and HOBT (125 mg) were added to a solution of (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylic acid (300 mg) in DMF (6 mL) at room temperature. 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 287 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-722965baade74aa09ac7245d3f8994ac
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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