1-Hydroxybenzotriazole → (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-(2-oxopiperidin-1-yl)acrylamide

HRID 546703Notes

Reaction equation

HRID 546703 reaction equation
C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.[NH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=[O:28].[CH3:29][O:30][C:31]1[CH:32]=[C:33](/[CH:43]=[CH:44]/[C:45](O)=[O:46])[CH:34]=[CH:35][C:36]=1[N:37]1[CH:41]=[C:40]([CH3:42])[N:39]=[CH:38]1>CN(C=O)C.O.C(OCC)(=O)C.C(Cl)CCl>[CH3:29][O:30][C:31]1[CH:32]=[C:33](/[CH:43]=[CH:44]/[C:45]([NH:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23]2=[O:28])=[O:46])[CH:34]=[CH:35][C:36]=1[N:37]1[CH:41]=[C:40]([CH3:42])[N:39]=[CH:38]1

Participants

9

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acidHCID 668394931-Aminopiperidin-2-one--hydrogen chloride (1/1)

Product 1

HCID 66839321(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]-N-(2-oxopiperidin-1-yl)acrylamide

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

IPEA (0.26 ml), HOBT (121 mg) and EDC (172 mg) were sequentially added to a suspension of 1-aminopiperidin-2-one hydrochloride (92 mg) and (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid (CAS No. 870839-41-1, 150 mg) in DMF (4 ml), and the reaction solution was stirred at room temperature overnight. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine. The combined aqueous layers were reextracted with ethyl acetate (twice). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was triturated with ethyl acetate to obtain 97 mg of the title compound. The property values of the compound are as follows.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-e97399b15782427faeac6bac087808bf
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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