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

HRID 80070노트

반응식

HRID 80070 반응식
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

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 68784637HCID 68784637, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-331ff0b8c8434e43ad7eed2270fe224d
출처 데이터셋
uspto-grants-2014_09
특허 번호
USRE045173E1

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