Triethylamine → HCID 67298422, compound

HRID 1520369Notes

Reaction equation

HRID 1520369 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[C:4]([C:15]2[CH:20]=[N:19][CH:18]=[CH:17][N:16]=2)[N:3]=1.[F:21][CH:22]([F:31])[O:23][C:24]1[CH:25]=[C:26]([NH2:30])[CH:27]=[CH:28][CH:29]=1.CCN(CC)CC>C1COCC1>[F:21][CH:22]([F:31])[O:23][C:24]1[CH:25]=[C:26]([NH:30][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[C:4]([C:15]3[CH:20]=[N:19][CH:18]=[CH:17][N:16]=3)[N:3]=2)[CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27741103-(Difluoromethoxy)anilineHCID 866770814-Chloro-6-nitro-2-(2-pyrazinyl)quinazoline

Product 1

HCID 67298422HCID 67298422, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-chloro-6-nitro-2-(pyrazin-2-yl)quinazoline (1.00 g, crude, 3.7 mmol, 1.0 eq.), 3-(difluoromethoxy)benzenamine (600 mg, 3.7 mmol, 1.0 eq.) and Et3N (1.00 g, 10 mmol, 3.0 eq) in THF (80 mL) was stirred at 75° C. for 18 h. After cooling, the volatiles were removed in vacuo and the residue was washed with H2O (100 mL×2). The solid was dried in vacuo to afford 1.40 g of N-(3-(difluoromethoxy)phenyl)-6-nitro-2-(pyrazin-2-yl)quinazolin-4-amine as a black solid (90.2% of two steps). LCMS m′ z=411.0 (M+1) (Method A) (retention time=1.61 min).

Workup

  1. temperatureAfter cooling
  2. customthe volatiles were removed in vacuo
  3. washthe residue was washed with H2O (100 mL×2)
  4. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-bdbc474009c24343a29016120ac73b69
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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