Hydrochloric Acid → HCID 178470358, compound

HRID 1696665Notes

Reaction equation

HRID 1696665 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[C:30]([CH3:35])=[CH:31][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[C:30]([CH3:35])=[CH:31][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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178470371HCID 178470371, compound

Product 1

HCID 178470358HCID 178470358, compoundYield 196.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

290 mg of 6-tert-butyloxy-9-[5-(5-chloro-7-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 137) are dissolved in 10 ml of dioxane and combined with 1.912 ml of 4N HCl in dioxane. The reaction mixture is stirred for 16 hours at room temperature. The formed insoluble material is collected by filtration, washed with dioxane (10 ml), diisopropylether (10 ml) and pentane (10 ml) and dried under vacuum to yield 268 mg of 9-[5-(5-chloro-7-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=93%. Analytical LC/MS (method B): m/z=524 (positive ion mode [M+H]+, 1 Cl present), m/z=522 (negative ion mode [M−H]−, 1 Cl present).

Workup

  1. filtrationThe formed insoluble material is collected by filtration
  2. washwashed with dioxane (10 ml), diisopropylether (10 ml) and pentane (10 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-33e6f07360e444bf98236f80a6ad0ca4
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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