Sodium Bicarbonate → HCID 178511961, compound

HRID 1186295Notes

Reaction equation

HRID 1186295 reaction equation
[N:1]1([CH2:6][CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=3)[NH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.I.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](SC)=[NH:25].C([O-])(O)=O.[Na+]>C(O)C>[N:1]1([CH2:6][CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:24]([C:20]4[S:19][CH:23]=[CH:22][CH:21]=4)=[NH:25])[CH:15]=3)[NH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 299237703-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-5-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511961HCID 178511961, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-5-amine (0.59 g, 2.57 mmol) in dry ethanol (10 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (1.467 g, 5.15 mmol) at room temperature and the resulting mixture was stirred overnight. The reaction was basified with saturated NaHCO3 solution (50 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined organic 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-(2-(pyrrolidin-1-yl)ethyl)-1H-indol-5-yl)thiophene-2-carboximidamide (0.39 g, 1.152 mmol, 44.8% yield) as a solid. 1H NMR (DMSO-d6) δ 10.59 (s, 1H), 7.70 (d, 1H, J=2.7 Hz), 7.58 (d, 1H, J=3.9 Hz), 7.26 (d, 1H, J=6.3 Hz), 7.10-7.08 (m, 2H), 6.92 (s, 1H), 6.62 (d, 1H, J=6.3 Hz), 6.23 (s, 2H), 2.80 (t, 2H, J=6.0 Hz), 2.65 (t, 2H, J=5.4 Hz), 2.52-2.48 (m, 4H, merged with DMSO peak), 1.68 (s, 4H); ESI-MS (m/z, %): 339 (MH+, 100).

Workup

  1. extractionwas extracted into CH2Cl2 (2×25 mL)
  2. washThe combined organic 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-aed51d0ec0fb49e2b83026875ad4b95a
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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