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

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:37]=[CH:36][C:13]([CH2:14][N:15]2[CH2:21][C:20]3[CH:22]=[C:23](/[CH:26]=[CH:27]/[C:28]([O:30]C(C)(C)C)=[O:29])[CH:24]=[N:25][C:19]=3[NH:18][C:17](=[O:35])[CH2:16]2)=[CH:12][CH:11]=1.[Cl:38]CCl>>[ClH:38].[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]2[CH2:21][C:20]3[CH:22]=[C:23](/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29])[CH:24]=[N:25][C:19]=3[NH:18][C:17](=[O:35])[CH2:16]2)=[CH:36][CH:37]=1

Participants

Reactant 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

Product 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

Procedure

Trifluoroacetic acid (1 mL) was added to a suspension of (E)-tert-butyl 3-(4(4-methoxybenzyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylate (112 mg, 0.27 mmol) in dichloromethane (1 mL) at room temperature. The reaction mixture was then stirred for 1 hour and concentrated to dryness. The resulting residue was suspended in a solution of hydrochloric acid in dioxane 4N (2 mL). After 10 minutes stirring at room temperature, the precipitate was filtered and washed with diethyl ether to afford the title product as a pale yellow solid (110 mg, quantitative).