4-(4-Benzoylpiperazin-1-yl)-2-nitrobenzoic acid → HCID 67185182, 화합물

HRID 1966457노트

반응식

HRID 1966457 반응식
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[C:17]([N+:24]([O-])=O)[CH:16]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.C1COCC1.[Pt]=O>[NH2:24][C:17]1[CH:16]=[C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:14][CH2:13]2)[CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20]

참가 물질

5

반응물 1

HCID 584256644-(4-Benzoylpiperazin-1-yl)-2-nitrobenzoic acid

생성물 1

HCID 67185182HCID 67185182, 화합물수율 70%

시약·촉매·용매 3

HCID 82844Platinum oxide (PtO)촉매HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

The obtained 4-(4-benzoylpiperazin-1-yl)-2-nitrobenzoic acid (0.40 g, 93%) was dissolved in 30 ml ethanol and 10 ml THF, followed by the addition of platinum oxide (20 mg, 5%) and stirred under hydrogen gas for 16 hours. The reaction was filtered with the aid of celite. 2-amino-4-(4-bezoylpiperazin-1-yl)benzoic acid (0.24 g, 70%) was obtained after removing of solvents. To a solution of 2-amino-4-(4-bezoylpiperazin-1-yl)benzoic acid (0.2 g, 0.6 mmol) and benzaldehyde (0.14 ml, 1.3 mmol) added sodium triacetoxyborohydride (0.4 g, 1.8 mmol) and stirred under argon atmosphere overnight. The reaction was quenched with 10 ml water and extracted with ethyl acetate (3×20 ml), followed by drying it over anhydrous sodium sulfate. 2-(benzylamino)-4-(4-benzoylpiperazin-1-yl)benzoic acid (0.11 g, 40%) was obtained after concentration. 1H NMR (500 MHz, CDCl3) δ (ppm) 3.25-3.88 (m, br, 8H), 4.48 (s, 2H), 6.20 (d, J=2.3 Hz, 1H), 6.22 (dd, J=2.3, 9.1 Hz, 1H), 7.30-7.45 (m, 10H), 7.48 (d, J=9.1 Hz, 1H), 8.25 (s, 1H), 10.65 (s, 1H).

후처리

  1. filtrationThe reaction was filtered with the aid of celite

출처 및 근거

ORD 기록
ord-593f55e1c22d4acb932d4c9e8edf2689
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420640B2

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