1,1'-Carbonyldiimidazole → 2-amino-N-(2,6-dioxo-piperidin-3-yl)-4-methyl-benzamide

HRID 453042

반응식

HRID 453042 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[NH2:25][CH:26]1[CH2:31][CH2:30][C:29](=[O:32])[NH:28][C:27]1=[O:33].C(=O)([O-])O.[Na+]>C(#N)C>[NH2:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:25][CH:26]1[CH2:31][CH2:30][C:29](=[O:32])[NH:28][C:27]1=[O:33])=[O:6]

참가 물질

6

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 753164-Methylanthranilic acidHCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 516892Sodium Bicarbonate

생성물 1

HCID 687315992-amino-N-(2,6-dioxo-piperidin-3-yl)-4-methyl-benzamide수율 70.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 2-amino-4-methylbenzoic acid (2.0 g, 13 mmol) and CDI (2.0 g, 12 mmol) in acetonitrile (20 mL) was stirred at room temperature for 1.5 hours. To the suspension, was added 3-amino-piperidine-2,6-dione hydrogen chloride (2.0 g, 12 mmol) and sodium hydrogen carbonate (1.3 g, 16 mmol), and the mixture was heated at 50° C. for 21 hours. The suspension was cooled to room temperature for 1 hour. The suspension was filtered and washed with water (50 mL) and ethyl acetate (20 mL). The solid was dried in a vacuum oven overnight to give 2-amino-N-(2,6-dioxo-piperidin-3-yl)-4-methyl-benzamide as a white solid (2.2 g, 69% yield): 1H NMR (DMSO-d6) δ 1.90-1.96 (m, 1H, CHH), 2.05-2.14 (m, 1H, CHH), 2.18 (s, 3H, CH3), 2.49-2.55 (m, 1H, Cull), 2.72-2.84 (m, 1H, CHH), 4.67-4.75 (m, 1H, NCH), 6.36 (dd, J=2, 8 Hz, 1H, Ar), 6.43 (br, 2H, NHH, Ar), 6.51 (s, 1H, NHH), 7.43 (d, J=8 Hz, 1H, Ar), 8.38 (d, J=8 Hz, 1H, NH), 10.83 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.05, 24.21, 30.99, 48.97, 111.26, 115.74, 116.48, 128.09, 141.71, 149.96, 168.54, 172.50, 173.04; LCMS: MH=262.

후처리

  1. temperaturethe mixture was heated at 50° C. for 21 hours
  2. temperatureThe suspension was cooled to room temperature for 1 hour
  3. filtrationThe suspension was filtered
  4. washwashed with water (50 mL) and ethyl acetate (20 mL)
  5. customThe solid was dried in a vacuum oven overnight

출처 및 근거

ORD 기록
ord-f672f4c76f074e8da965ed93a7ef4f81
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492395B2

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