Dimethylformamide → HCID 18919130, compound

HRID 1291429Notes

Reaction equation

HRID 1291429 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([C:11]2[CH:31]=[CH:30][C:14]([CH2:15][S:16][C:17]3[N:26]([CH3:27])[C:25](=[O:28])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][C:23]=4[CH3:29])[N:18]=3)=[CH:13][CH:12]=2)=[O:10])[CH2:5][CH2:4]1.Cl.[CH2:33](Cl)[C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1.C(N(CC)CC)C.CN(C=[O:52])C>>[CH3:27][N:26]1[C:25](=[O:28])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[CH3:29])[N:18]=[C:17]1[S:16][CH2:15][C:14]1[CH:13]=[CH:12][C:11]([C:9]([N:6]2[CH2:5][CH2:4][CH:3]([CH2:2][O:1][C:33](=[O:52])[C:34]3[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=3)[CH2:8][CH2:7]2)=[O:10])=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 745704-(Chloromethyl)pyridinium chlorideHCID 18918806HCID 18918806, compound

Product 1

HCID 18919130HCID 18919130, compound

Procedure

In DMF (15 ml) was dissolved 2-[4-(4-hydroxymethylpiperidylcarbonyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (415 mg), and following addition of isonicotinyl chloride hydrochloride (270 mg), triethylamine (0.40 ml) was added over 5 minutes. The mixture was stirred at room temperature for 3 hours, after which it was concentrated. The residue was washed with water, saturated aqueous NaHCO3 solution, and saturated aqueous NaCl solution in that order, dried, and concentrated. The residue was recrystallized from hexane/ethyl acetate to provide the title compound as colorless solid (241 mg).

Workup

  1. additionwas added over 5 minutes
  2. concentrationafter which it was concentrated
  3. washThe residue was washed with water, saturated aqueous NaHCO3 solution, and saturated aqueous NaCl solution in that order
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-93c8e46287b74ad29482fec09cfc3283
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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