HCID 57421478, compound → HCID 178422092, compound

HRID 1668451Notes

Reaction equation

HRID 1668451 reaction equation
[CH3:1][C:2]1[N:3]([CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([NH2:11])=[CH:6][CH:5]=2.I.CS[C:22]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)=[NH:23]>C(O)C.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[N:3]([CH2:12][CH2:13][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([NH:11][C:22]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)=[NH:23])=[CH:6][CH:5]=2

Participants

5

Reactant 2

HCID 57421478HCID 57421478, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178422092HCID 178422092, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of compound 27 (0.37 g, 1.520 mmol) in dry ethanol (5 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.86 g, 3.040 mmol) at room temperature and stirred for overnight (16 h). The reaction was diluted with sat. NaHCO3 solution (25 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer was washed with brine (15 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95) to obtain compound 28 (0.43 g, 81%) as a foam. 1H NMR (DMSO-d6) δ 1.64-1.76 (m, 4H), 2.39 (s, 3H), 2.46-2.58 (m, 4H), 2.66 (t, 2H, J=7.2 Hz), 4.16 (t, 2H, J=7.2 Hz), 6.09 (s, 1H), 6.20 (brs, 2H), 6.61 (dd, 1H, J=1.8, 8.5 Hz), 6.87 (d, 1H, J=1.2 Hz), 7.08 (dd, 1H, J=3.9, 4.9 Hz), 7.27 (d, 1H, J=8.7 Hz), 7.57 (d, 1H, J=5.4 Hz), 7.70 (d, 1H, J=3.6 Hz); ESI-MS (m/z, %) 253 (MH+, 100), 177 (56); ESI-HRMS calculated for C20H25N4S (MH+), calculated: 353.1794; observed: 353.1804; HPLC purity: 97% by area.

Workup

  1. extractionwas extracted into CH2Cl2 (2×25 mL)
  2. washThe combined CH2Cl2 layer was washed with brine (15 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-e57f67694e704f549d843cce91ee294e
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

Loading…