3-Methylbenzoic acid → HCID 24963673, 화합물

HRID 1868276노트

반응식

HRID 1868276 반응식
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([OH:9])=O)[CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:24][CH2:25][C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[C:28](=[O:45])[N:29]([CH:37]1[CH2:42][CH2:41][C:40](=[O:43])[NH:39][C:38]1=[O:44])[C:30]([CH3:36])=[N:31]2>CN(C=O)C>[O:44]=[C:38]1[CH:37]([N:29]2[C:28](=[O:45])[C:27]3[C:32](=[CH:33][CH:34]=[CH:35][C:26]=3[CH2:25][NH:24][C:7](=[O:9])[C:3]3[CH:4]=[CH:5][CH:6]=[C:1]([CH3:10])[CH:2]=3)[N:31]=[C:30]2[CH3:36])[CH2:42][CH2:41][C:40](=[O:43])[NH:39]1

참가 물질

5

반응물 3

HCID 74183-Methylbenzoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 249683051015474-47-1

생성물 1

HCID 24963673HCID 24963673, 화합물수율 76%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of m-toluic acid (0.24 g, 1.8 mmol) in DMF (8 mL) in a 40° C. oil bath, was added 1.1′ carbonyldiimidazole (0.31 g, 1.9 mmol) and stirred for one hour. To the mixture, 3-(5-aminomethyl-2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione hydrogen chloride (0.59 g, 1.8 mmol) was added, and the mixture was stirred for 45 minutes. The solvent was evaporated, and the residue was purified by flash column chromatography (Silica gel, methanol/methylene chloride 4%/96%) to give N-[3-(2,6-dioxo-piperidin-3-yl)-2-methyl-4-oxo-3,4-dihydro-quinazolin-5-ylmethyl]-3-methyl-benzamide as a light green solid (560 mg, 76% yield); HPLC, Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 10/90 CH3CN/0.1% H3PO4, grad. to 95/5 in 5 min, kept 5 min, 6.00 min (99.2%); mp, 263-265° C.; 1HNMR (DMSO-d6) 2.18-2.21 (m, 1H, CHH), 2.38 (s, 3H, CH3Ar), 2.59-2.88 (m, 6H, CHCH2, CH3), 4.95-5.12 (m, 2H, CH2NH), 5.26 (dd, J=6, 11 Hz, 1H, CH), 7.33-7.76 (m, 7H, Ar), 8.89 (t, J=5 Hz, 1H, CH2NH), 11.05 (s, 1H, NH); 13C NMR (DMSO-d6) δ 20.83, 20.92, 23.29, 30.60, 42.12, 56.52, 117.65, 123.98, 124.32, 125.40, 127.76, 128.26, 131.85, 133.93, 134.23, 137.65, 141.04, 148.50, 154.80, 161.11, 166.39, 169.53, 172.61. LCMS MH=419; Anal Calcd For C23H22N4O4+0.6H2O: C, 64.36; H, 5.45; N, 13.05. Found: C, 64.36; H, 5.24; N, 13.22.

후처리

  1. stirringthe mixture was stirred for 45 minutes
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash column chromatography (Silica gel, methanol/methylene chloride 4%/96%)

출처 및 근거

ORD 기록
ord-2bee1e246b3f43628056842e170cdced
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635700B2

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