HCID 67335335, compound → HCID 59382798, compound

HRID 1675218Notes

Reaction equation

HRID 1675218 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:31][CH2:32][CH2:33][CH2:34][N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)=[C:25]([N+:28]([O-])=O)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1>C(O)(=O)C.C(OC(=O)C)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:31][CH2:32][CH2:33][CH2:34][N:35]4[CH2:36][CH2:37][O:38][CH2:39][CH2:40]4)=[C:25]([NH2:28])[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

5

Reactant 1

HCID 67335335HCID 67335335, compound

Product 1

HCID 59382798HCID 59382798, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

353 mg of iron dissolved in aqueous 5% acetic acid solution was activated at 100° C. 450 mg of [3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-[7 (3-morpholin-4-yl-propoxy)-6-nitro-quinazolin-4-yl]-amine (see, Journal of Medicinal Chemistry 2000, 43, 1380) dissolved in a mixture of ethylacetate and acetic acid (1:1) was added thereto dropwise, and refluxed. The hot reacted solution was filtered under a reduced pressure through celite pad, and the pad was washed with ethylacetate. The washed solvent was washed with saturated sodium bicarbonate solution several times. The organic layer was dried over magnesium sulfate, and filtered and distilled under a reduced pressure to obtain the title compound (353 mg, 83%).

Workup

  1. customwas activated at 100° C
  2. additionwas added
  3. temperaturedropwise, and refluxed
  4. filtrationThe hot reacted solution was filtered under a reduced pressure through celite pad
  5. washthe pad was washed with ethylacetate
  6. washThe washed solvent was washed with saturated sodium bicarbonate solution several times
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-214ad747a1f341d8bd081a26de23f8fc
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

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