Hydrochloric Acid → HCID 67278064, compound
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]2[CH:18]([C:19]3[O:20][C:21]([S:24][C:25]4[NH:29][C:28]5[CH:30]=[C:31]([CH3:35])[C:32]([Cl:34])=[CH:33][C:27]=5[N:26]=4)=[CH:22][CH:23]=3)[C:17]3[C:16](=[O:36])[CH2:15][N:14](OC(C)(C)C)[CH2:13][C:12]=3[NH:11][C:10]=12)=[O:5])[CH3:2].Cl>O1CCOCC1>[ClH:34].[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]2[CH:18]([C:19]3[O:20][C:21]([S:24][C:25]4[NH:29][C:28]5[CH:30]=[C:31]([CH3:35])[C:32]([Cl:34])=[CH:33][C:27]=5[N:26]=4)=[CH:22][CH:23]=3)[C:17]3[C:16](=[O:36])[CH2:15][NH:14][CH2:13][C:12]=3[NH:11][C:10]=12)=[O:5])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
328 mg 6-tert-butyloxy-9-[5-(5-chloro-6-methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-2,4,5,7,8,9-hexahydro-pyrrolo[3,4-b]-1,7-naphthyridine-3-carboxylic acid ethyl ester (example 134) are dissolved in 10 ml of dioxane and combined with 2.16 ml of 4N HCl in dioxane. The mixture is stirred for 16 hours at room temperature. The insoluble material is collected by filtration, washed with dioxane (10 ml), diisopropylether (10 ml) and pentane (10 ml) and dried under vacuum to yield 290 mg of 9-[5-(5-chloro-6-methyl-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]-1,7-naphthyridine-3-carboxylic acid ethyl ester hydrochloride. Yield=98%. Analytical LC/MS: m/z=524 (positive ion mode [M+H]+, 1 Cl present), m/z=522 (negative ion mode [M−H]−, 1 Cl present)
Workup
- filtrationThe insoluble material is collected by filtration
- washwashed with dioxane (10 ml), diisopropylether (10 ml) and pentane (10 ml)
- customdried under vacuum
Sources & evidence
- ORD record
- ord-9c30e1acf2094ebba4d15151ecfe95f9
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163768B2
Reaction notes
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