Dichloromethane → (E)-3-(4-(4-Methoxybenzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride

反応式

C([O:5][C:6](=[O:30])/[CH:7]=[CH:8]/[C:9]1[CH:29]=[N:28][C:12]2[NH:13][C:14](=[O:27])[CH2:15][N:16]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH2:17][C:11]=2[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:39]>>[ClH:39].[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:16]2[CH2:17][C:11]3[CH:10]=[C:9](/[CH:8]=[CH:7]/[C:6]([OH:30])=[O:5])[CH:29]=[N:28][C:12]=3[NH:13][C:14](=[O:27])[CH2:15]2)=[CH:24][CH:23]=1

参加物

反応物 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 59456913(E)-3-[4-(4-Methoxy-benzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid tert-butyl ester

生成物 1

HCID 66966837(E)-3-(4-(4-Methoxybenzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride収率 92%

実験手順

A suspension of (E)-3-[4-(4-methoxy-benzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid tert-butyl ester (3.54 g, 8.65 mmol) in CH2Cl2 (20 mL) was treated with TFA (20 mL). After stirring at room temperature under N2 for 25 min, the clear tan solution was concentrated in vacuo. The resulting residue was treated with anhydrous HCl (40 mL of a 4.0 M solution in dioxane, 160 mmol) and sonicated for 15 min. The solid was isolated by filtration, washed with Et2O and dried under vacuum at 50° C. for 3 d to give the title compound (3.40 g, 92%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 12.38 (br s, 1H), 11.32 (s, 1H), 8.77 (s, 1H), 8.28 (s, 1H), 7.66-7.58 (m, 3H), 7.02 (d, J=8.6 Hz, 2H), 6.63 (d, J=16.1 Hz, 1H), 4.41-4.27 (m, 5H), 3.79 (s, 3H), 3.68 (s, 2H); MS (ESI) m/e 354 (M+H)+.