Sodium hydride → HCID 53922765, compound

HRID 1264237Notes

Reaction equation

HRID 1264237 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15](=[O:18])[NH:14][N:13]=2)=[CH:8][CH:7]=1.Cl.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]Cl>CS(C)=O>[CH3:3][O:4][C:5](=[O:19])[C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15](=[O:18])[N:14]([CH2:24][CH2:23][N:22]([CH3:26])[CH3:21])[N:13]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 53863116HCID 53863116, compound

Product 1

HCID 53922765HCID 53922765, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
50 °C

Procedure

To DMSO (3.5 mL) is added 60% NaH dipersion in mineral oil (84 mg, 2.1 mmol) and the resulting mixture stirred for 5 min. To this solution is added 4-(6-oxo-1,6-dihydro-pyridazin-3-yl)-benzoic acid methyl ester (460 mg, 2 mmol reference example 36e) and the mixture stirred for 10 min (till homogeneous). In a separate flask containing DMSO (3.5 mL) is added 60% NaH (101 mg, 2.5 mmol) and stirred 5 min. To this solution is added 2-dimethylaminoethylchloride hydrochloride (346 mg, 2.4 mmol) and let stir for 5 min. This solution is transferred to the reaction solution, heated to 50° C., let stir for 2 hours. Cooled to 20° C., quenched with sat NH4Cl soln (2 mL) and concentrated. The residue is purified by short path flash chromatography (eluting with 10% methanol in dichloromethane) to give 542 mg of title compound. 1H NMR (CD3OD) δ 2.35 (s, 6H), 2.88 (t, J=7 Hz, 2H), 3.93 (s, 3H), 4.42 (t, J=7 Hz, 2H), 7.08 (d, J=10 Hz, 1H), 8.06 (m, 5H). MS (EI) m/z 302 (M+H)+.

Workup

  1. stirringthe mixture stirred for 10 min (till homogeneous)
  2. stirringstirred 5 min
  3. stirringlet stir for 5 min
  4. stirringlet stir for 2 hours
  5. temperatureCooled to 20° C.
  6. customquenched with sat NH4Cl soln (2 mL)
  7. concentrationconcentrated
  8. customThe residue is purified by short path flash chromatography (eluting with 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-b15ea42f5af14e68a0d2cfc1622bbd21
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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