2-Chloroquinazoline → HCID 57662924, compound

HRID 1515210Notes

Reaction equation

HRID 1515210 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[N:17]([C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:30])[C:16]2=[O:31]>C(O)CCC>[CH3:29][C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:30])[C:23]=1[N:17]1[C:16](=[O:31])[C:15]2[C:19](=[CH:20][CH:21]=[C:13]([NH:12][C:2]3[N:11]=[C:10]([C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=3)[CH:14]=2)[C:18]1=[O:22]

Participants

4

Reactant 2

HCID 740542-ChloroquinazolineHCID 1240314-Amino-N-(2,6-dimethylphenyl)phthalimide

Product 1

HCID 57662924HCID 57662924, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of 2-chloroquinazoline (0.62 g, 2.6 mmol) and 5-amino-2-(2,6-dimethylphenyl)isoindoline-1,3-dione (0.69 g, 2.6 mmol) in n-butanol (10 mL) was heated at 120° C. until all of the butanol had evaporated. Additional butanol (10 mL) was added and the process repeated twice. After the reaction mixture was cooled, water was added (20 mL). A precipitate which formed was collected by suction filtration. N,N-Dimethylacetamide (5 mL) was added to dissolve the solid which was purified by preparative reverse-phase HPLC to give 2-(2,6-dimethylphenyl)-5-[(4-phenylquinazolin-2-yl)amino]-1H-isoindole-1,3(2H)-dione (0.26 g, 21%). 1H NMR (400 MHz, DMSO-d6): δ 10.88 (s, 1H), 8.80 (m, 1H), 8.42 (m, 1H), 7.96 (m, 1H), 7.90 (m, 2H), 7.85 (m, 1H), 7.81 (m, 2H), 7.65 (m, 3H), 7.50 (m, 1H), 7.32 (m, 1H), 7.25 (m, 2H), 2.10 (s, 6H). MS (EI) for C30H22N4O2: 471.0 (MH+).

Workup

  1. customhad evaporated
  2. additionAdditional butanol (10 mL) was added
  3. temperatureAfter the reaction mixture was cooled
  4. additionwater was added (20 mL)
  5. customA precipitate which formed
  6. filtrationwas collected by suction filtration
  7. additionN,N-Dimethylacetamide (5 mL) was added
  8. dissolutionto dissolve the solid which
  9. customwas purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-66691234508445f390b18692870f1765
Source dataset
uspto-grants-2012_07
Patent number
US08222263B2

Reaction notes

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