Hydrochloric Acid → HCID 178470367, compound

HRID 1696653Notes

Reaction equation

HRID 1696653 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][CH:35]([F:37])[F:36])=[CH:33][C:27]=5[N:26]=4)=[CH:22][CH:23]=3)[C:17]3[C:16](=[O:38])[CH2:15][N:14](OC(C)(C)C)[CH2:13][C:12]=3[NH:11][C:10]=12)=[O:5])[CH3:2].[ClH:44]>O1CCOCC1>[ClH:44].[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][CH:35]([F:37])[F:36])=[CH:33][C:27]=5[N:26]=4)=[CH:22][CH:23]=3)[C:17]3[C:16](=[O:38])[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 178470376HCID 178470376, compound

Product 1

HCID 178470367HCID 178470367, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

230 mg of 6-tert-butyloxy-9-[5-(5-difluoromethoxy-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 127) are dissolved in 1.4 ml of dioxane and combined with 1.434 ml of 4N HCl in dioxane. The reaction mixture is stirred for 16 hours at room temperature. The formed insoluble material is then collected by filtration, washed successively with 2×2 ml of dioxane and 2×2 ml of diisopropylether, and dried under vacuum to yield 107 mg of 9-[5-(5-difluoromethoxy-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 brown powder. Yield=55%. Analytical LC/MS (method B): retention time=2.90 min., m/z=541.96 (positive ion mode).

Workup

  1. filtrationThe formed insoluble material is then collected by filtration
  2. washwashed successively with 2×2 ml of dioxane and 2×2 ml of diisopropylether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-4daf8c85c3544cdd99665f08f25c80d3
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

Loading…