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2-Dimethylaminopyridine → [1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl]-carbamic acid benzyl ester

HRID 221302
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HRID 221302 반응식
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].O=C1CCC(=O)N1O[C:26](=O)[CH:27]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:28][CH3:29].CN(C1C=CC=CN=1)C.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[CH2:34]([O:33][C:31](=[O:32])[NH:30][CH:27]([C:26]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4](=[O:5])[C:3]2[C:2](=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:17])[N:1]=1)[CH2:28][CH3:29])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
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참가 물질

6

반응물 4

HCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 12961228(2,5-Dioxopyrrolidin-1-yl) 2-(phenylmethoxycarbonylamino)butanoateHCID 167877862-Amino-6-methyl-N-phenylbenzamide

생성물 1

HCID 59841071[1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl]-carbamic acid benzyl ester

시약·촉매·용매 1

HCID 1140
Toluene
용매

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온도
110 °C

실험 절차

Compound 15 (1.20 g, 5.30 mmol) was combined with 2-benzyloxycarbonylaminobutyric acid 2,5-dioxo-pyrrolidin-1-yl ester (2.13 g, 6.36 mmol), dimethylaminopyridine (915 mg, 7.49 mmol), and diisopropylethylamine (1.10 mL, 6.36 mmol) in toluene (15 mL). The mixture was heated to 110° C. and stirred at that temperature for 22 hours. After cooling, the reaction was purified by flash chromatography to provide the quinazolinone (16) as a pale yellow solid. MS (ES): m/z 428 (M+H). 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 7.75 (d, 2H, J=7.9 Hz), 7.32 (t, 2H, J=7.8 Hz), 7.07 (t, 1H, J=7.3 Hz), 7.00 (t, 1H, J=7.8 Hz), 6.58 (d, 1H, J=8.1 Hz), 6.46 (d, 1H, J=7.4 Hz), 4.98 (br. s, 2H), 2.21 (s, 3H). The reaction described above and compound 16 are shown below.

후처리

  1. temperatureAfter cooling
  2. customthe reaction was purified by flash chromatography

출처 및 근거

ORD 기록
ord-a8143a2410f740e1a785e466404ed1e6
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08207153B2

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