Water → HCID 21290286, compound

HRID 867746Notes

Reaction equation

HRID 867746 reaction equation
[CH2:1]([C:3]1[C:8]([OH:9])=[N:7][C:6]([CH3:10])=[C:5]2[S:11][CH:12]=[CH:13][C:4]=12)[CH3:2].[H-].[Na+].Cl.[CH3:17][N:18]([CH2:20][CH2:21]Cl)[CH3:19].O>CN(C=O)C>[CH2:1]([C:3]1[C:8]([O:9][CH2:21][CH2:20][N:18]([CH3:19])[CH3:17])=[N:7][C:6]([CH3:10])=[C:5]2[S:11][CH:12]=[CH:13][C:4]=12)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 178437337HCID 178437337, compound

Product 1

HCID 21290286HCID 21290286, compoundYield 110.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Ethyl-7-methylthieno[2,3-c]pyridin-5-ol (2.00 g, 10.3 mmol) was added to a suspension of NaH (60% in oil, prewashed with hexanes, 0.46 g, 11.4 mmol) in DMF (30 ml) and stirred at room temperature for two hours. To this was added a mixture of dimethylaminoethylchloride hydrochloride (3.0 g, 20.6 mmol) and NaH (60% in oil, prewashed with hexanes, 546 mg, 22.8 mmol) in DMF (30 ml). The reaction mixture was stirred for two days at room temperature, poured into H2O (300 ml) and extracted with CH2Cl2 (3×200 ml). The combined organic phases were washed with H2O (2×200 ml) and dried over MgSO4. The solvent was removed in vacuo to give an oil (3 g), which was purified by flash chromatography on silica gel 60 (100 g) eluted with 7% MeOH in CH2Cl2 to give an oil (1.5 g, 56% yield). The product was dissolved in CH2Cl2 (100 ml), washed with 1N aqueous NaOH (2×100 ml) and dried over MgSO4. The solvent was removed in vacuo to give the product (0.950 g, 35% yield) as a yellow oil; IR (neat) 1590 and 1440 cm-1 ; mass spectrum m/z 264 (M+); 1H NMR (CDCl3) δ 1.18 (t, J=7 Hz, 3H, CH2CH3), 2.35 (s, 6H, N(CH3)2), 2.63 (s, 3H, 7-CH3), 2.63-3.10 (m, 4H, CH2CH2N, CH2CH3), 4.53 (t, J=6 Hz, 2H, CH2CH2N), 7.27 and 7.53 each (d, J=5 Hz, 1H, thiophene-H).

Workup

  1. additionTo this was added
  2. stirringThe reaction mixture was stirred for two days at room temperature
  3. extractionextracted with CH2Cl2 (3×200 ml)
  4. washThe combined organic phases were washed with H2O (2×200 ml)
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-57e36646d3cf4315865534d79b82b885
Source dataset
uspto-grants-1988_10
Patent number
US04775757

Reaction notes

Loading…