HCID 11160262, compound → HCID 178422093, compound

HRID 1668449Notes

Reaction equation

HRID 1668449 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:15].I.CS[C:20]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[NH:21]>C(O)C.C([O-])(O)=O.[Na+]>[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH:14][C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[NH:21])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:15]

Participants

5

Reactant 2

HCID 11160262HCID 11160262, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178422093HCID 178422093, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of compound 24 (0.275 g, 1.266 mmol) in dry ethanol (5 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.72 g, 2.532 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 25 (0.32 g, 78%) as a foam. 1H NMR (DMSO-d6) δ 2.22 (s, 6H), 2.39 (s, 3H), 2.46-2.51 (m, 2H, merged with DMSO peak), 4.14 (t, 2H, J=6.9 Hz), 6.09 (s, 1H), 6.20 (brs, 2H), 6.61 (dd, 1H, J=1.2, 8.4 Hz), 6.87 (s, 1H), 7.09 (t, 1H, J=4.2 Hz), 7.27 (d, 1H, J=8.7 Hz), 7.57 (d, 1H, J=5.1 Hz), 7.70 (d, 1H, J=3.3 Hz); ESI-MS (m/z, %) 327 (MH+, 100); ESI-HRMS calculated for C18H23N4S (MH+), calculated: 327.1637; observed: 327.1653; HPLC purity: 98% 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-5616675450b74804906071bb771fd932
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

Loading…