Water → HCID 21290302, compound

HRID 867745Notes

Reaction equation

HRID 867745 reaction equation
Cl.[CH3:2][N:3]([CH2:5][CH2:6][CH2:7]Cl)[CH3:4].[H-].[Na+].[CH2:11]([C:13]1[C:18]([OH:19])=[N:17][C:16]([CH3:20])=[C:15]2[S:21][CH:22]=[CH:23][C:14]=12)[CH3:12].O>CN(C=O)C>[CH2:11]([C:13]1[C:18]([O:19][CH2:7][CH2:6][CH2:5][N:3]([CH3:4])[CH3:2])=[N:17][C:16]([CH3:20])=[C:15]2[S:21][CH:22]=[CH:23][C:14]=12)[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 178437337HCID 178437337, compound

Product 1

HCID 21290302HCID 21290302, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-(N,N-Dimethylamino)propylchloride hydrochloride (5.51 g, 34.9 mmol) and sodium hydride (60% in oil, 1.55 g, 38.8 mmol, prewashed with pentane) in DMF (30 ml) were stirred at room temperature for one hour. This solution was then added to a mixture of 4-ethyl-7-methylthieno[2,3-c]pyridin-5-ol (2.9 g, 15.0 mmol) and sodium hydride (60% in oil, 0.60 g, 15.0 mmol, prewashed in pentane) in DMF (30 ml) which had been allowed to react for two hours. The combination was stirred at room temperature for three days, poured into H2O (500 ml), extracted with CH2Cl2 (3×200 ml) and dried over MgSO4. The solvent was removed in vacuo and the product was purified by flash chromatography on silica gel 60 (120 g) using 8% MeOH in CH2Cl2 as the eluant to give the product (2.3 g, 55% yield) as a yellow oil; IR (neat) 1440, 1580 and 2980 cm-1 ; mass spectrum m/z 279 (MH+); 1H NMR (CDCl3) δ 1.20 (t, J=7 Hz, 3H, CH2CH3), 1.68 to 2.90 (m, 6H, CH2CH2N, CH2CH3), 2.27 (s, 6H, N(CH3)2), 2.63 (s, 3H, 7-CH3), 4.43 (t, J=6 Hz, 1H, OCH2CH2), 7.27 and 7.53 each (d, J=6 Hz, 1H, thiophene-H).

Workup

  1. customto react for two hours
  2. extractionextracted with CH2Cl2 (3×200 ml)
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customthe product was purified by flash chromatography on silica gel 60 (120 g)

Sources & evidence

ORD record
ord-c27cc9e2f3af44bf8740e98fac891042
Source dataset
uspto-grants-1988_10
Patent number
US04775757

Reaction notes

Loading…