1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-Methyl-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzamide

HRID 2383754ノート

反応式

HRID 2383754 の反応式
C[CH2:2][N:3]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.CN.[CH3:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][C:36]=1[N:41]1[CH2:45][CH2:44][N:43]([C:46]2[CH:54]=[CH:53][C:49]([C:50]([OH:52])=O)=[CH:48][CH:47]=2)[C:42]1=[O:55]>CN(C=O)C>[CH3:2][NH:3][C:50](=[O:52])[C:49]1[CH:48]=[CH:47][C:46]([N:43]2[CH2:44][CH2:45][N:41]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][C:35]=3[CH3:34])[C:42]2=[O:55])=[CH:54][CH:53]=1

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 68784637HCID 68784637、化合物

生成物 1

HCID 59636255N-Methyl-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzamide収率 65.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDCI (176.4 mg, 0.9205 mmol), HOBt (5.8 mg, 0.2525 mmol), DIPEA (0.3 mL, 2.3006 mmol) and methylamine hydrochloride (62 mg, 0.9205 mmol) were added to a stirred solution of 4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid (228 mg, 0.7668 mmol) in dry DMF (10 mL) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was partitioned between water and ethylacetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel (5% MeOH in DCM) afforded 155 mg of the product (65.4% yield).

後処理

  1. customThe reaction mixture was partitioned between water and ethylacetate
  2. washThe organic layer was washed with water, brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography on silica gel (5% MeOH in DCM)

出典と根拠

ORDレコード
ord-3e5863201bc34226ae9d92534d90ed5f
出典データセット
uspto-grants-2012_09
特許番号
US08263635B2

反応ノート

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