2-Chloroquinazoline → HCID 57662924, compound

HRID 406845

Reaction equation

HRID 406845 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-314e9a87e0de4aa19734bdec3432787e
Source dataset
uspto-grants-2014_06
Patent number
US08754092B2

Linked notes

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