Water → 3-(2-ethyl-5-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione

HRID 1409609

반응식

HRID 1409609 반응식
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:3]=1[C:4]([NH:6][CH:7]1[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:8]1=[O:14])=[O:5].[C:20](OCC)(OCC)(OCC)[CH2:21][CH3:22].O>CN(C=O)C.CO>[CH2:21]([C:22]1[N:6]([CH:7]2[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:8]2=[O:14])[C:4](=[O:5])[C:3]2[C:2](=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:19])[N:1]=1)[CH3:20]

참가 물질

6

반응물 3

HCID 962WaterHCID 66995Ethyl orthopropionateHCID 659566542-amino-N-(2,6-dioxo-piperidin-3-yl)-6-methyl-benzamide

생성물 1

HCID 249675953-(2-ethyl-5-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione수율 22.9%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 2-amino-N-(2,6-dioxo-piperidin-3-yl)-6-methyl-benzamide (0.5 g, 1.9 mmol) and triethyl orthopropionate (0.42 mL, 2.1 mmol) in DMF (5 mL) was heated at 150° C. in a microwave oven for 1.5 hours. To the mixture, was added water (30 mL). The mixture was cooled in an ice-water bath. The suspension was filtered to give a solid, which was stirred in methanol (15 mL) overnight. The suspension was filtered and washed with methanol (10 mL) and ethyl acetate (10 mL) to give 3-(2-ethyl-5-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione as a white solid (0.13 g, 22% yield): HPLC: Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 10/90 grad 90/10 in 5 min CH3CN/0.1% H3PO4, 5.74 min (98.9%); mp: 228-230° C.; 1H NMR (DMSO-d6) δ 1.27 (t, J=7 Hz, 3H, CH3), 2.07-2.13 (m, 1H, CHH), 2.50 (s, 3H, CH3), 2.51-2.65 (m, 2H, 2CHH), 2.82-2.92 (m, 3H, CH2, CHH), 5.21 (dd, J=6, 11 Hz, 1H, NCH), 7.25 (d, J=8 Hz, 1H, Ar), 7.46 (d, J=8 Hz, 1H, Ar), 7.64 (t, J=8 Hz, 1H, Ar), 10.98 (s, 1H, NH); 13C NMR (DMSO-d6) δ 11.18, 21.05, 22.48, 28.02, 35.51, 55.26, 118.64, 125.00, 128.86, 133.70, 139.82, 148.27, 157.69, 161.14, 169.75, 172.63; LCMS: MH=300; Anal Calcd for C16H17N3O3: C, 64.20; H, 5.72; N, 14.04. Found: C, 61.30; H, 5.34; N, 13.28.

후처리

  1. temperatureThe mixture was cooled in an ice-water bath
  2. filtrationThe suspension was filtered
  3. customto give a solid, which
  4. filtrationThe suspension was filtered
  5. washwashed with methanol (10 mL) and ethyl acetate (10 mL)

출처 및 근거

ORD 기록
ord-d4409ac14c4243c1b7b55246138c4be8
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921385B2

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