3-(2,6-Dichlorophenyl)-4-formyl-5-isoxazolecarbonyl chloride → 3-(2,6-Dichlorophenyl)-N-(5-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}pentyl)-5-methyl-4-isoxazolecarboxamide

HRID 1832234노트

반응식

HRID 1832234 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH:14]=[O:15])=[C:12]([C:16](Cl)=O)[O:11][N:10]=1.[NH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([C:31]2[CH:32]=[C:33]([NH:37][C:38](=[O:43])[CH:39]([CH2:41]C)[CH3:40])[CH:34]=[CH:35][CH:36]=2)[CH2:27][CH2:26]1>C1COCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([C:14]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]2[CH2:26][CH2:27][CH:28]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([NH:37][C:38](=[O:43])[CH:39]([CH3:40])[CH3:41])[CH:32]=3)[CH2:29][CH2:30]2)=[O:15])=[C:12]([CH3:16])[O:11][N:10]=1

참가 물질

4

반응물 2

HCID 220486823-(2,6-Dichlorophenyl)-4-formyl-5-isoxazolecarbonyl chlorideHCID 22048959N-{3-[1-(5-aminopentyl)-4-piperidinyl]phenyl}-2-ethylpropanamide

생성물 1

HCID 220487233-(2,6-Dichlorophenyl)-N-(5-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}pentyl)-5-methyl-4-isoxazolecarboxamide수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 3-(2,6-dichlorophenyl)-4-formyl-5-isoxazolecarbonyl chloride (69.0 mg, 0.250 mmol), N-{3-[1-(5-aminopentyl)-4-piperidinyl]phenyl}-2-ethylpropanamide (44.0 mg, 0.150 mmol), TEA (30.0 mg, 0.300 mmol) in THF (2 mL) was stirred for 12 h at room temperature. The crude product was purified by preparative TLC using CH2Cl2/MeOH/isopropyl amine (19:1:0.2) to give the desired product (52 mg, 67%). 1H NMR (400 MHz, CDCl3) δ 7.52–7.49 (m, 2H), 7.49–7.41 (m, 2H), 7.39–7.31 (m, 2H), 7.29–7.21 (m, 2H), 6.92 (d, 1H, J=7.6 Hz), 3.25–3.11 (m, 5H), 2.81–2.74 (m, 4H), 2.58–2.44 (m, 4H), 2.30–2.19 (m, 2H), 1.93–1.78 (m, 4H), 1.56–1.44 (m, 2H), 1.31–1.28 (m, 2H), 1.24 (d, 6H, J=6.6 Hz); ESMS m/e: 585.2 (M+H)+.

후처리

  1. customThe crude product was purified by preparative TLC

출처 및 근거

ORD 기록
ord-d48c7118d5854dabbb4e494064a4e9f4
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067534B1

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