Hydrochloric Acid → HCID 178470362, compound

HRID 1696671Notes

Reaction equation

HRID 1696671 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]([F:35])=[CH:31][C:32]([F: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].[ClH:42]>O1CCOCC1>[ClH:42].[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]([F:35])=[CH:31][C:32]([F: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 178470373HCID 178470373, compound

Product 1

HCID 178470362HCID 178470362, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 300 mg of 6-tert-butyloxy-9-[5-(5,7-difluoro-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 in 10 ml of dioxane is combined with 1.8 ml of 4N HCl in dioxane and the reaction mixture is stirred for 16 hours at room temperature. The formed insoluble material is collected by filtration, washed with dioxane (70 ml), pentane (50 ml), diisopropylether (50 ml) and dried under vacuum to yield 227 mg of 9-[5-(5,7-difluoro-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 light brown powder. Yield=84%. Analytical LC/MS (method C): m/z=511 (negative ion mode [M−H]−), m/z=512 (positive ion mode [M+H]+) 500 MHz 1H NMR on a BRUKER AVANCE DRX-500 spectrometer, chemical shifts (δ in ppm) in d6 dimethylsufoxyde (DMSO-d6) solvent referenced at 2.50 ppm at 303K temperature: 1.28 (t, J=7.0 Hz, 3H); 3.72 (d broad, J=16.0 Hz, 1H); 3.81 (m, 1H); 4.22 (m, 1H); 4.28 (q, J=7.0 Hz, 2H); 4.45 (d broad, J=16.0 Hz, 1H); 5.20 (s, 1H); 6.40 (d, J=3.5 Hz, 1H); 6.85 (d, J=3.5 Hz, 1H); 6.90 (d, J=3.5 Hz, 1H); 7.06 (dt, J=2.0 et 11.0 Hz, 1H); 7.17 (dd, J=2.0 et8.5 Hz, 1H); 9.39 (s, 1H); 10.1 (m broad, 1H); 10.4 (m broad, 1H); 11.65 (d, J=3.5 Hz, 1H).

Workup

  1. filtrationThe formed insoluble material is collected by filtration
  2. washwashed with dioxane (70 ml), pentane (50 ml), diisopropylether (50 ml)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-0dc504c33833424393702610c0b8b4a9
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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