HCID 56593710, compound → HCID 178511902, compound

HRID 1668492Notes

Reaction equation

HRID 1668492 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH:18]4[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]4)[CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O.I.CS[C:24]([C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)=[NH:25]>C(O)C.[Pd]>[N:15]12[CH2:20][CH2:19][CH:18]([CH2:17][CH2:16]1)[CH:13]([C:8]1[C:7]3[C:11](=[CH:12][C:4]([NH:1][C:24]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[NH:25])=[CH:5][CH:6]=3)[NH:10][CH:9]=1)[CH2:14]2

Participants

5

Reactant 2

HCID 56593710HCID 56593710, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511902HCID 178511902, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Compound 109 (0.4 g, 1.485 mmol) in dry ethanol (10 mL) was treated with Pd—C (˜0.05 g), purged with hydrogen gas and stirred for 36 h at room temperature under hydrogen atm (balloon pressure). The reaction was filtered through celite bed and washed with ethanol (2×5 mL). The combined ethanol layer was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.84 g, 2.970 mmol) at room temperature and stirred for over night (14 h). The solvent was evaporated, crude was diluted with sat. NaHCO3 solution (25 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer washed with brine (20 mL) and dried (Na2SO4). The solvent was evaporated and crude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9) to obtain compound 112 (0.4 g, 77%) as a solid. mp 144-146° C.; 1H NMR (DMSO-d6) δ 1.20-1.28 (m, 1H), 1.56-1.74 (m, 3H), 2.62-2.72 (m, 1H), 2.79-2.92 (m, 3H), 3.09-3.34 (m, 4H), 6.30 (s, 2H), 6.53 (d, 1H, J=8.4 Hz), 6.79 (s, 1H), 7.07-7.10 (m, 2H), 7.38 (d, 1H, J=8.4 Hz), 7.58 (d, 1H, J=4.5 Hz), 7.72 (d, 1H, J=3.0 Hz), 10.61 (s, 1H); ESI-MS (m/z, %): 351 (MH+, 38), 176 (100); ESI-HRMS calculated for C20H23N4S (MH+), calculated: 351.1637; observed: 351.1637.

Workup

  1. custompurged with hydrogen gas
  2. filtrationThe reaction was filtered through celite bed
  3. washwashed with ethanol (2×5 mL)
  4. stirringstirred for over night (14 h)
  5. customThe solvent was evaporated
  6. additioncrude was diluted with sat. NaHCO3 solution (25 mL) and product
  7. extractionwas extracted into CH2Cl2 (2×25 mL)
  8. washThe combined CH2Cl2 layer washed with brine (20 mL)
  9. dry with materialdried (Na2SO4)
  10. customThe solvent was evaporated
  11. customcrude was purified by column chromatography (2M NH3 in MeOH:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-b0e7e19516ef4a84b39f3aa0bdccd2ce
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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