Sodium Bicarbonate → HCID 178511960, compound

HRID 1186292Notes

Reaction equation

HRID 1186292 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][OH:19])[CH2:13][CH:12]=1.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27].C([O-])(O)=O.[Na+]>C(O)C>[OH:19][CH2:18][CH2:17][N:14]1[CH2:15][CH:16]=[C:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:26]([C:22]4[S:21][CH:25]=[CH:24][CH:23]=4)=[NH:27])[CH:3]=3)[NH:7][CH:6]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 577918722-(4-(5-amino-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanolHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511960HCID 178511960, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-(5-amino-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanol (0.16 g, 0.622 mmol) in dry ethanol (5 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.355 g, 1.244 mmol) at room temperature and stirred overnight (18 h). The reaction was basified with sat. NaHCO3 solution (50 mL) and product was extracted into CH2Cl2 (3×20 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-(2-hydroxyethyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl)thiophene-2-carboximidamide (0.14 g, 61.4%) as a solid. 1H NMR (DMSO-d6) δ 10.92 (s, 1H), 7.71 (d, 1H, J=3.6 Hz), 7.58 (d, 1H, J=5.1 Hz), 7.33-7.30 (m, 2H), 7.21 (s, 1H), 7.09 (t, 1H, J=3.9 Hz), 6.66 (d, 1H, J=8.4 Hz), 6.23 (brs, 2H), 6.03 (s, 1H), 4.40 (t, 1H, J=5.1 Hz), 3.54 (q, 2H), 3.16-3.10 (m, 2H), 2.66 (t, 2H, J=5.4 Hz), 2.50-2.44 (m, 4H, merged with DMSO-peak); ESI-MS (m/z, %): 367 (MH+, 33), 294 (100).

Workup

  1. extractionwas extracted into CH2Cl2 (3×20 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-f3a01419f2fa4952ace7554606a14754
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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