Hydrochloric Acid → HCID 178470369, compound

HRID 1696682Notes

Reaction equation

HRID 1696682 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]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:33][C:27]=5[N:26]=4)=[CH:22][CH:23]=3)[C:17]3[C:16](=[O:39])[CH2:15][N:14](OC(C)(C)C)[CH2:13][C:12]=3[NH:11][C:10]=12)=[O:5])[CH3:2].[ClH:45]>O1CCOCC1>[ClH:45].[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]([O:34][C:35]([F:38])([F:36])[F:37])=[CH:33][C:27]=5[N:26]=4)=[CH:22][CH:23]=3)[C:17]3[C:16](=[O:39])[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 178470377HCID 178470377, compound

Product 1

HCID 178470369HCID 178470369, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 6-tert-butyloxy-8-oxo-9-[5-(5-trifluoromethoxy-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-2,4,5,7,8,9-hexahydro-pyrrolo[3,4-b][1,7]naphthyridine-3-carboxylic acid ethyl ester (0.65 g, 0.98 mmol) in dioxane (20 ml) is combined with 4N HCl in dioxane (3.57 ml). The reaction mixture is stirred at room temperature for 16 hours. The formed insoluble material is collected by filtration, washed with dioxane (100 ml), pentane (50 ml) and dried under vacuum to yield 350 mg of 8-oxo-9-[5-(5-trifluoromethoxy-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-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=64%. Analytical LC/MS (method C): m/z=558 (negative ion mode [M−H]−), m/z=560 (positive ion mode [M+H]+).

Workup

  1. filtrationThe formed insoluble material is collected by filtration
  2. washwashed with dioxane (100 ml), pentane (50 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-28d2feb44bc5453da1c0065613aba72a
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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