Dichloromethane → HCID 178511915, compound

HRID 1668486Notes

Reaction equation

HRID 1668486 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([NH2:18])=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](SC)=[NH:26].ClCCl>C(O)C.C(=O)(O)[O-].[Na+]>[N:1]1([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([NH:18][C:25]([C:21]4[S:20][CH:24]=[CH:23][CH:22]=4)=[NH:26])=[CH:15][CH:16]=3)[CH:11]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 11447902HCID 11447902, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511915HCID 178511915, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of compound 95 (0.200 mg, 0.822 mmol) in absolute ethanol (3 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.350 g, 1.23 mmol) at room temperature and the resulting mixture was stirred for 3 hours. The reaction was diluted with saturated aqueous sodium bicarbonate (5 mL) followed by dichloromethane (30 mL) and transferred to a separatory funnel. The aqueous was extracted twice more with dichloromethane (2×30 mL). The combined organics were washed with brine and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M ammonia in methanol:dichloromethane, 5:95) to obtain compound 96 (130 mg, 45%) as a yellow oil. 1H NMR (CDCl3) δ 7.43 (d, J=2.7 Hz, 1H), 7.41 (s, 1H), 7.34 (d, J=8.7 Hz, 1H), 7.21 (d, J=1.2 Hz, 1H), 7.14 (d, J=3.0 Hz, 1H), 7.08 (t, J=4.2 Hz, 1H), 6.67 (dd, J=1.8, 8.7 Hz, 1H), 6.42 (d, J=3.0 Hz, 1H), 4.24 (t, J=7.5 Hz, 2H), 2.73 (t, J=7.5 Hz, 2H), 2.47 (m, 4H), 1.61 (m, 4H); ESI-MS (m/z, %): 353 (M+1); ESI-HRMS calculated for C20H25N4S (MH+): 353.1794, Observed: 353.1796.

Workup

  1. customtransferred to a separatory funnel
  2. extractionThe aqueous was extracted twice more with dichloromethane (2×30 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customSolvent was evaporated
  6. customcrude was purified by column chromatography (2M ammonia in methanol:dichloromethane, 5:95)

Sources & evidence

ORD record
ord-2383b4c930f740bbaa9c8347f39cfd04
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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