1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal → 2-[4-(1-Methyl-1-pyridin-2-yl-ethylamino)-butyl]-isoindole-1,3-dione

HRID 251079

반응식

HRID 251079 반응식
[CH3:1][C:2]([NH2:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:3].[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[CH2:22][CH2:23][CH2:24][CH:25]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:1][C:2]([NH:10][CH2:25][CH2:24][CH2:23][CH2:22][N:13]1[C:14](=[O:21])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]1=[O:11])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH3:3]

참가 물질

4

반응물 3

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 5049666Sodium triacetoxyborohydrideHCID 227369222-(2-Pyridyl)-2-propylamine

생성물 1

HCID 672731322-[4-(1-Methyl-1-pyridin-2-yl-ethylamino)-butyl]-isoindole-1,3-dione

실험 절차

Using General Procedure B, reaction of 1-methyl-1-pyridin-2-yl-ethylamine (Chakravarty, P K et al. Bioorg. Med. Chem. Lett. 2003, 13, 147-150) with 4-(1,3-Dioxo-1,3-dihydroisoindole-2-yl)-butyraldehyde and NaBH(OAc)3 gave 2-[4-(1-methyl-1-pyridin-2-yl-ethylamino)-butyl]-isoindole-1,3-dione as a colorless oil. 1H NMR (CDCl3) δ 1.46 (s, 6H), 1.50-1.56 (m, 2H), 1.60-1.74 (m, 2H), 2.31 (t, 2H, J=7.0 Hz), 3.65 (t, 2H, J=7.1 Hz), 7.07-7.14 (m, 1H), 7.39 (d, 1H, J=8.3 Hz), 7.63 (td, 1H, J=7.7, 1.8 Hz), 7.66-7.74 (m, 2H), 7.77-7.87 (m, 2H), 8.56 (d, 1H, J=3.9 Hz).

출처 및 근거

ORD 기록
ord-488a270a3b5a4ec6b76c36d8eabeddb2
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863293B2

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