N-methyl-2-pyrrolidone → HCID 478661, compound

HRID 1756582Notes

Reaction equation

HRID 1756582 reaction equation
Cl[C:2]1[CH:18]=[C:17]2[C:5]([C:6](=[O:20])[C:7]3[N:16]2[C:15](=[O:19])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=3)=[CH:4][CH:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.CN1C(=O)CCC1>C(Cl)(Cl)Cl>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]2[CH:18]=[C:17]3[C:5]([C:6](=[O:20])[C:7]4[N:16]3[C:15](=[O:19])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=4)=[CH:4][CH:3]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 531671-MethylpiperazineHCID 3362709-Chloroindolo[2,1-b]quinazoline-6,12-dione

Product 1

HCID 478661HCID 478661, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9-Chloroindolo[2,1-b]quinazoline-6,12-dione (Example 31, 155 mg, 0.55 mmol), N-methylpiperazine (75 μL, 0.68 mmol) and 3 mL of NMP were stirred at at 70° C. for 1 h. Chloroform (50 mL) was added and the mixture was washed with water (3×100 mL), dried (Na2SO4), filtered and solvent removed in vacuo to give the crude product. Silica gel chromatography purification of the residue using (95:5) chloroform:methanol as eluent gave 101 mg (53%) of the title compound: mp 214° C. (dec); 1H NMR(CDCl3) δ 2.40 (s, 3H), 2.55-2.65 (m, 4H), 3.60-3.70 (m, 4H), 6.68-6.74 (dd, 1H), 760-7.70 (t, 1H), 7.73-7.80 (m, 1H), 7.80-7.86 (m, 1H), 7.99-8.05 (d, 1H), 8.10-8.14(d, 1H), 8.36-8.42 (d, 1H); MS (M+H)+ 347.2.

Workup

  1. washthe mixture was washed with water (3×100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customsolvent removed in vacuo
  5. customto give the crude product
  6. customSilica gel chromatography purification of the residue

Sources & evidence

ORD record
ord-4b37a597d5334bb6b3a13d03b3751777
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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