HCID 59004615, compound → HCID 178422091, compound

HRID 1668453Notes

Reaction equation

HRID 1668453 reaction equation
[CH3:1][C:2]1[N:3]([CH2:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH3:19])[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([NH2:11])=[CH:6][CH:5]=2.I.CS[C:23]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)=[NH:24]>C(O)C.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[N:3]([CH2:12][CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][N:15]2[CH3:19])[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([NH:11][C:23]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)=[NH:24])=[CH:6][CH:5]=2

Participants

5

Reactant 2

HCID 59004615HCID 59004615, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178422091HCID 178422091, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of compound 31 (0.32 g, 1.243 mmol) in dry ethanol (10 mL) was treated with thiophene-2-carboximidothioic acid methyl ester hydroiodide (0.7 g, 2.486 mmol) at room temperature and stirred for 4 h. The reaction was diluted with sat. NaHCO3 solution (25 mL) and product was extracted into CH2Cl2 (2 25 mL). The combined CH2Cl2 layer 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 32 (0.45 g, 99%) as a foam. 1H NMR (DMSO-d6) δ 1.48-1.68 (m, 4H), 1.87-1.98 (m, 2H), 2.01-2.18 (m, 2H), 2.22 (s, 3H), 2.39 (s, 3H), 2.92-2.98 (m, 1H), 4.07 (t, 2H, J=7.8 Hz), 6.09 (s, 1H), 6.19 (brs, 2H), 6.62 (dd, 1H, J=1.5, 8.5 Hz), 6.87 (s, 1H), 7.08 (dd, 1H, J=3.6, 4.9 Hz), 7.26 (d, 1H, J=8.4 Hz), 7.57 (d, 1H, J=5.4 Hz), 7.70 (d, 1H, J=3.6 Hz); ESI-MS (m/z, %) 367 (MH+, 62), 184 (100), 126 (37); ESI-HRMS calculated for C21H27N4S (MH+), calculated: 367.1950, observed: 367.1965; HPLC purity: 96.2% by area.

Workup

  1. extractionwas extracted into CH2Cl2 (2 25 mL)
  2. washThe combined CH2Cl2 layer 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-ed216499632046478fa9a8e30752a698
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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