1,2-Dichloroethane → N-[2-(cyclopropylamino)-4-fluorophenyl]-5-fluoropyridine-3-carboxamide

HRID 1048961노트

반응식

HRID 1048961 반응식
[CH:1]1([NH:4][C:5]2[C:6]([NH2:12])=[CH:7][CH:8]=[C:9]([F:11])[CH:10]=2)[CH2:3][CH2:2]1.[F:13][C:14]1[CH:15]=[C:16]([C:20](O)=[O:21])[CH:17]=[N:18][CH:19]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH:1]1([NH:4][C:5]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=2[NH:12][C:20]([C:16]2[CH:17]=[N:18][CH:19]=[C:14]([F:13])[CH:15]=2)=[O:21])[CH2:3][CH2:2]1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1202325-Fluoronicotinic AcidHCID 545925541-N-cyclopropyl-5-fluorobenzene-1,2-diamine

생성물 1

HCID 66692355N-[2-(cyclopropylamino)-4-fluorophenyl]-5-fluoropyridine-3-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of the title compound from N2-cyclopropyl-4-fluorobenzene-1,2-diamine (0.065 g, 0.39 mmol) in dichloromethane (1.96 mL) were added 5-fluoropyridine-3-carboxylic acid (0.061 g, 0.43 mmol), EDC (0.082 g, 0.43 mmol), HOBt (0.066 g, 0.43 mmol), and diisopropylethylamine (0.280 mL, 1.56 mmol). The reaction was stirred at room temperature overnight, then diluted with dichloromethane, washed sequentially with water and brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (30-50% ethyl acetate in hexanes) provided the title compound: LCMS m/z 290.14 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.90 (s, 1 H), 8.66 (d, J=2.0 Hz, 1 H), 7.97 (d, J=8.3 Hz, 1 H), 7.48 (br s, 1 H), 7.19 (m, 1 H), 6.92 (d, J=10.9 Hz, 1 H), 6.52-6.49 (m, 1 H), 4.50 (br s, 1 H), 2.47-2.44 (m, 1 H), 0.81-0.77 (m, 2 H), 0.54-0.51 (m, 2 H).

출처 및 근거

ORD 기록
ord-1110bdac77eb4afbba235a0d1bdf549f
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382226B2

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