Hydrochloric Acid → HCID 60207449, compound

HRID 1192226Notes

Reaction equation

HRID 1192226 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([C:15]1[S:16][C:17]([S:23][C:24]2[C:29]([Cl:30])=[CH:28][N:27]=[CH:26][C:25]=2[Cl:31])=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)=[O:14])(C(C)(C)C)(C)C.Cl>CCOCC.O>[Cl:30][C:29]1[CH:28]=[N:27][CH:26]=[C:25]([Cl:31])[C:24]=1[S:23][C:17]1[S:16][C:15]([C:13]([NH:12][CH2:11][CH2:10][CH2:9][OH:8])=[O:14])=[CH:19][C:18]=1[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 60207448HCID 60207448, compound

Product 1

HCID 60207449HCID 60207449, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

N-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-((3,5-dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxamide (1.0 g, 1.92 mmol) from the above was added to a solution of hydrogen chloride in ether (2.0 M, 15 mL) and dry ether (15 mL), and the resulting mixture was stirred at ambient temperature for 1 hour. After this time, the reaction mixture was diluted with water, extracted with ethyl acetate and washed with brine and water. The organic layer was separated, dried (Na2SO4) and concentrated. The crude residue was purified by silica gel chromatography using a 97:3 mixture of dichloromethane and methanol as eluent to afford the title product as a solid (550 mg, 37% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.99 (2H, s), 8.81 (1H, m), 8.43 (1H, s), 3.41 (2H, m), 3.24 (2H, m), 1.61 (2H, m).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine and water
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by silica gel chromatography
  7. additiona 97:3 mixture of dichloromethane and methanol as eluent

Sources & evidence

ORD record
ord-b820a18220df4297a6a4a4e8f454160d
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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