Sodium Bicarbonate → HCID 178462533, compound

HRID 1186271Notes

Reaction equation

HRID 1186271 reaction equation
[CH2:1]([N:3]1[CH2:8][CH:7]=[C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=3)[NH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].I.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](SC)=[NH:26].C([O-])(O)=O.[Na+]>C(O)C>[CH2:1]([N:3]1[CH2:4][CH:5]=[C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:25]([C:21]4[S:20][CH:24]=[CH:23][CH:22]=4)=[NH:26])[CH:16]=3)[NH:11][CH:10]=2)[CH2:7][CH2:8]1)[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22611536HCID 22611536, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178462533HCID 178462533, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-amine (0.32 g, 1.326 mmol) in dry ethanol (10 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.756 g, 2.65 mmol) at room temperature and stirred overnight (18 h). The reaction was basified with sat. NaHCO3 solution (30 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9) to obtain N-(3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiophene-2-carboximidamide (0.37 g, 80%) as a solid. 1H NMR (DMSO-d6) δ 10.94 (s, 1H), 7.71 (d, 1H, J=3.3 Hz), 7.59 (s, 1H, J=5.1 Hz), 7.31 (dd, 1H, J=2.7, 5.4 Hz), 7.22 (s, 1H), 7.10 (t, 1H, J=4.8 Hz), 6.67 (d, 1H, J=8.4 Hz), 6.26 (brs, 2H), 6.05 (s, 1H), 3.10 (brs, 2H), 2.63 (t, 2H, J=5.1 Hz), 2.54-2.40 (m, 4H, merged with DMSO-peak), 1.06 (t, 3H, J=7.2 Hz); ESI-MS (m/z, %): 351 (MH+, 37), 294 (100); ESI-HRMS calculated for C20H23N4S (MH+), calculated: 351.1637; observed: 351.1636.

Workup

  1. extractionwas extracted into CH2Cl2 (2×25 mL)
  2. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customSolvent was evaporated
  5. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-ab7d86826b664028bc25e5895e8aae2e
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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