Hydrochloric Acid → HCID 67278509, compound

HRID 1696668Notes

Reaction equation

HRID 1696668 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:26][C:27]5[CH:33]=[C:32]6[O:34][C:35]([F:38])([F:37])[O:36][C:31]6=[CH:30][C:28]=5[N:29]=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:26][C:27]5[CH:33]=[C:32]6[O:34][C:35]([F:38])([F:37])[O:36][C:31]6=[CH:30][C:28]=5[N:29]=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 67277944HCID 67277944, compound

Product 1

HCID 67278509HCID 67278509, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

170 mg of 6-tert-butyloxy-9-[5-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-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 140) are dissolved in 10 ml of dioxane and combined with 0.94 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), diisopropyl ether (10 ml) and pentane (10 ml) and dried under vacuum to yield 150 mg of 9-[5-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-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=98%. Analytical LC/MS (method B): m/z=554 (negative ion mode [M−H]−), m/z=556 (positive ion mode [M+H]+)

Workup

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

Sources & evidence

ORD record
ord-ad38ee21c3bd49ab971f584614ae0f8e
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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