HCID 59004643, compound → HCID 178480324, compound

HRID 1668490Notes

Reaction equation

HRID 1668490 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1.I.CS[C:21]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)=[NH:22]>C(O)C>[NH3:2].[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:21]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[NH:22])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1

Participants

5

Reactant 2

HCID 59004643HCID 59004643, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 2

HCID 222AmmoniaHCID 178480324HCID 178480324, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

compound 103 (65 mg, 0.283 mmol) is charged to a small, argon purged flask fitted with a magnetic stir bar. Anhydrous ethanol (7 mL) and thiophene-2-carboximidothioic acid methyl ester hydroiodide (121.2 mg, 0.425 mmol) are added to the flask and the reaction was stirred under argon at ambient temperature for 17 hours, at which time the solvent was evaporated and the residue was partitioned between H2O and ethyl acetate and 1M sodium hydroxide solution added to adjust pH to 9. The mixture was transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered, concentrated and the residue purified via chromatography on silica gel (MeOH:CH2Cl2, 1:9 then 2M NH3 in MeOH:CH2Cl2, 5:95 to 1:9) to yield compound 104 (30 mg, 31.3%) as a yellow solid. 1H NMR (DMSO-d6) δ 1.47-1.76 (m, 4H), 2.16 (q, 1H, J=8.5 Hz), 2.25 (s, 3H), 2.50-2.59 (m, 1H), 2.92-3.02 (m, 1H), 3.97 (dd, 1H, J=14.1, 7.1 Hz), 4.23 (dd, 1H, J=14.0, 4.8 Hz), 6.23 (brs, 2H), 6.31 (d, 1H, J=3.0 Hz), 6.69 (d, 1H, J=8.3 Hz), 6.98 (s, 1H), 7.08-7.11 (m, 1H), 7.31 (d, 1H, J=3.0 Hz), 7.39 (d, 1H, J=8.6 Hz), 7.58 (d, 1H, J=5.2 Hz), 7.71 (d, 1H, J=3.7 Hz); ESI-MS (m/z, %): 339 (MH+, 100%); ESI-HRMS calculated for C19H23N4S (MH+): 339.1637, observed: 339.1653.

Workup

  1. customfitted with a magnetic stir bar
  2. customwas evaporated
  3. customthe residue was partitioned between H2O and ethyl acetate and 1M sodium hydroxide solution
  4. additionadded
  5. customThe mixture was transferred to a separatory funnel
  6. customthe organic layer collected
  7. extractionThe aqueous layer was further extracted with ethyl acetate
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customthe residue purified via chromatography on silica gel (MeOH

Sources & evidence

ORD record
ord-49a8db3a5a7c41479353c3da88c82a52
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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