4-Chloro-2-phenylquinazoline → HCID 59426459, compound

HRID 252587Notes

Reaction equation

HRID 252587 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:21][CH3:22])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=3)=[CH:4][CH:3]=1.Cl[C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[C:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:25]=1.C(N(C(C)C)CC)(C)C>C(O)C>[CH2:21]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[CH:11]=2)[C:16]([C:17]#[N:18])=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=[C:26]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:25]=2)=[CH:7][CH:6]=1)[CH3:22]

Participants

5

Reactant 3

HCID 809774-Chloro-2-phenylquinazolineHCID 81531DiisopropylethylamineHCID 11601736HCID 11601736, compound

Product 1

HCID 59426459HCID 59426459, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-aminophenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (100 mg, 0.343 mmol), 4-chloro-2-phenyl-quinazoline (83 mg, 0.34 mmol) and diisopropylethylamine (0.10 mL, 0.57 mmol) in absolute ethanol (3 mL) is heated to reflux overnight. The solution is cooled and evaporated, and the residue taken up in ethyl acetate (50 mL). This is washed with water and saturated brine (50 mL each), then dried over anhydrous sodium sulfate, filtered and evaporated. The resulting solid is triturated with ether, collected by filtration and dried under vacuum to afford 1-ethyl-6-methoxy-2-[4-(2-phenylquinazolin-4-ylamino)-phenyl]-1H-indole-3-carbonitrile (139 mg, 0.280 mmol, 82%).

Workup

  1. temperatureto reflux overnight
  2. temperatureThe solution is cooled
  3. customevaporated
  4. washThis is washed with water and saturated brine (50 mL each)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid is triturated with ether
  9. filtrationcollected by filtration
  10. customdried under vacuum

Sources & evidence

ORD record
ord-9b5f41e9a00c4410b7ccc81e7c9613dc
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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