p-Toluenesulfonic acid → 3-(7-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione

HRID 509504

反応式

HRID 509504 の反応式
[NH2:1][C:2]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][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]1(C)C=CC(S(O)(=O)=O)=CC=1>C(OC)(OC)OC>[CH3:19][C:17]1[CH:18]=[C:2]2[C:3]([C:4](=[O:5])[N:6]([CH:7]3[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:8]3=[O:14])[CH:20]=[N:1]2)=[CH:15][CH:16]=1

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 687315992-amino-N-(2,6-dioxo-piperidin-3-yl)-4-methyl-benzamide

生成物 1

HCID 252359113-(7-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione収率 223.4%

試薬・触媒・溶媒 1

HCID 9005Trimethyl orthoformate溶媒

実験手順

A solution of 2-amino-N-(2,6-dioxo-piperidin-3-yl)-4-methyl-benzamide (1.0 g, 3.8 mmol) and trimethyl orthoformate (10 mL) and p-toluene sulfonic acid (250 mg) was heated to 160° C. in a microwave oven for 30 minutes. The suspension was filtered and washed with methanol (20 mL), water (20 mL) and methanol (20 mL) to give 3-(7-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione as an off-white solid (880 mg, 85% yield): HPLC: Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 20/80 CF3CN/0.1% H3PO4, 5.14 min (97.1%); mp: 313-315° C.; 1H NMR (DMSO-d6) δ 2.11-2.18 (m, 1H, CHH), 2.48 (s, 3H, CH), 2.61-2.74 (m, 2H, 2CHH), 2.82-2.92 (m, 1H, CHH), 5.46 (br, 1H. NCH), 7.41 (dd, J=1, 8 Hz, 1H, Ar), 7.53 (s, 1H, Ar), 8.03 (d, J=8 Hz, 1H, Ar), 8.33 (s, 1H, CH), 11.15 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.23, 22.51, 30.91, 56.74, 118.95, 125.93, 126.74, 128.66, 145.27, 147.35, 147.59, 159.54, 169.88, 172.44; LCMS: MH=272; Anal Calcd for C14H13N3O3+0.1H2O: C, 61.58; H, 4.87; N, 15.39. Found: C, 61.41; H, 4.87; N, 15.15.

後処理

  1. filtrationThe suspension was filtered
  2. washwashed with methanol (20 mL), water (20 mL) and methanol (20 mL)

出典と根拠

ORDレコード
ord-8bd4e9326b5e4671aa905cf6bcdaaa38
出典データセット
uspto-grants-2015_08
特許番号
US09096573B2

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