HCID 59004667, compound → HCID 178480391, compound

HRID 1668474Notes

Reaction equation

HRID 1668474 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)[CH2:4][CH2:3]1.I.CS[C:21]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)=[NH:22]>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([NH:17][C:21]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[NH:22])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 59004667HCID 59004667, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178480391HCID 178480391, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 81 (100 mg, 0.436 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 (217.6 mg, 0.763 mmol) are added to the flask and the reaction was stirred under argon at ambient temperature for 23 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 (2M NH3 in methanol:CH2Cl2, 5:95 to 7.5:92.5) to yield a yellow solid, 82 (83 mg, 56.2%). 1H NMR (DMSO-d6) δ 1.85-2.05 (m, 4H), 2.10-2.19 (m, 2H), 2.24 (s, 3H), 2.90 (d, 2H, J=11.4 Hz), 4.20-4.32 (m, 1H), 6.25 (br s, 2H), 6.35 (d, 1H, J=3.0 Hz), 6.69 (dd, 1H, J=9.8, 1.4 Hz), 6.98 (s, 1H), 7.07-7.10 (m, 1H), 7.41 (d, 1H, J=3.1 Hz), 7.45 (d, 1H, J=8.7 Hz), 7.59 (d, 1H, J=5.1 Hz), 7.71 (d, 1H, J=3.1 Hz); ESI-MS (m/z, %): 339 (MH+, 100%); ESI-HRMS calculated for C19H23N4S (MH+): 339.1637, observed: 339.1647.

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 (2M NH3 in methanol:CH2Cl2, 5:95 to 7.5:92.5)

Sources & evidence

ORD record
ord-90a71e8ea3694526a999eec1f83fdecb
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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