Hydrochloric Acid → HCID 178470363, compound

HRID 1696675Notes

Reaction equation

HRID 1696675 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]([Cl:35])[C:32]([F: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:35].[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]([Cl:35])[C:32]([F: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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178470374HCID 178470374, compound

Product 1

HCID 178470363HCID 178470363, compoundYield 183.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 6-tert-butyloxy-9-[5-(6-chloro-5-fluoro-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 (0.376 g, 0.60 mmol) in dioxane (20 ml) is combined with 4 N HCl in dioxane (2.17 ml) and the mixture is stirred at room temperature for 16 hours. The formed insoluble material is collected by filtration, washed with dioxane (40 ml), pentane (40 ml), diisopropylether (40 ml) and dried under vacuum to yield 310 mg of 9-[5-(6-chloro-5-fluoro-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 as a light brown powder. Yield=92%. Analytical LC/MS (method B): m/z=528 (positive ion mode, [M+H]+, 1 Cl present), m/z=526 (negative ion mode [M−H]−, 1 Cl present)

Workup

  1. filtrationThe formed insoluble material is collected by filtration
  2. washwashed with dioxane (40 ml), pentane (40 ml), diisopropylether (40 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-fd4f5f003b9c4073bcd378dcf7a4af99
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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