Hydrochloric Acid → HCID 178470360, compound

HRID 1696678Notes

Reaction equation

HRID 1696678 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]([F: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]([F: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 178470372HCID 178470372, compound

Product 1

HCID 178470360HCID 178470360, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 6-tert-butyloxy-9-[5-(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 (0.380 g, 0.64 mmol) in dioxane (20 ml) is combined with 4 N HCl in dioxane (2.32 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 323 mg of 9-[5-(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 orange-brown powder. Yield=95%. Analytical LC/MS method B: m/z=492 (negative ion mode [M−H]−), m/z=494 (positive ion mode [M+H]+).

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-f665ac8479604c378ddf2f045421a08b
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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