Hydrochloric Acid → HCID 178470357, compound

HRID 1696656Notes

Reaction equation

HRID 1696656 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]([Cl: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].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[CH:30]=[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: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 178470370HCID 178470370, compound

Product 1

HCID 178470357HCID 178470357, compoundYield 137%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

210 mg of 6-tert-butyloxy-9-[5-(5-chloro-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 130) are dissolved in 1.4 ml of dioxane and combined with 1.415 ml of 4N HCl in dioxane. The reaction mixture is stirred for 16 hours at room temparature. The formed insoluble material is then collected by filtration, washed with 2×1 ml of dioxane and 2×1 ml of diisopropylether. The residue is then purified on a silica gel column (12 g) eluted with a mixture of dichloromethane and methanol (95/5, v/v). The fraction containing the expected product are concentrated under reduced pressure to yield 135 mg of 9-[5-(5-chloro-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 an orange powder. Yield=77%. Analytical LC/MS (method B): m/z=508 (negative ion mode, [M−H]−, 1 Cl present), m/z=510 (positive ion mode, [M+H]+)

Workup

  1. filtrationThe formed insoluble material is then collected by filtration
  2. washwashed with 2×1 ml of dioxane and 2×1 ml of diisopropylether
  3. customThe residue is then purified on a silica gel column (12 g)
  4. washeluted with a mixture of dichloromethane and methanol (95/5
  5. additionThe fraction containing the expected product
  6. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-568050c7de344005b5dc949b07204fb5
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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