Hydrochloric Acid → HCID 178470365, compound

HRID 1696649Notes

Reaction equation

HRID 1696649 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]=[CH:31][C:32]([OH:34])=[CH:33][C:27]=5[N:26]=4)=[CH:22][CH:23]=3)[C:17]3[C:16](=[O:35])[CH2:15][N:14](OC(C)(C)C)[CH2:13][C:12]=3[NH:11][C:10]=12)=[O:5])[CH3:2].[ClH:41]>O1CCOCC1>[ClH:41].[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]=[CH:31][C:32]([OH:34])=[CH:33][C:27]=5[N:26]=4)=[CH:22][CH:23]=3)[C:17]3[C:16](=[O:35])[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 178470375HCID 178470375, compound

Product 1

HCID 178470365HCID 178470365, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 6-tert-butyloxy-9-[5-(5-hydroxy-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 (0.27 g, 0.46 mmol) in dioxane (20 ml) is combined with 4N HCl in dioxane (1.7 ml). The reaction mixture is stirred at room temperature for 16 hours. The formed insoluble material is collected by filtration, washed with dioxane (50 ml), pentane (20 ml), diisopropylether (20 ml) and dried under vacuum to yield 176 mg of 9-[5-(5-hydroxy-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 white powder. Yield=73%. Analytical L/MS (method C): m/z=490 (negative ion mode [M−H]−), m/z=492 (positive ion mode [M+H]+).

Workup

  1. filtrationThe formed insoluble material is collected by filtration
  2. washwashed with dioxane (50 ml), pentane (20 ml), diisopropylether (20 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d51c0f8cbc2c4303b6fa4fca9ade3df2
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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