Acetic Acid → Allitinib metabolite M6

HRID 1666237

Reaction equation

HRID 1666237 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[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>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[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

4

Reactant 2

HCID 176Acetic AcidHCID 536304764-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-6-nitro-quinazoline

Product 1

HCID 53630477Allitinib metabolite M6Yield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

In a flask equipped with a reflux condenser, the compound obtained in Example 6 1.60 g (3.77 mmol), reduced iron powder 1.05 g (18.85 mmol, 5 eq), glacial acetic acid (2 mL) and methanol (40 mL) were mixed. The mixture was refluxed in an oil bath at a temperature of 85° C. for 2.5 h. Then the iron powder was filtered of, the filtrate was diluted with ethyl acetate, washed sequentially with NaHCO3 solution and water. The organic phase was dried and concentrated to obtain yellow solid, which was identified as the title compound. Yield: 61%.

Workup

  1. customIn a flask equipped with a reflux condenser
  2. filtrationThen the iron powder was filtered of, the filtrate
  3. additionwas diluted with ethyl acetate
  4. washwashed sequentially with NaHCO3 solution and water
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. customto obtain yellow solid, which

Sources & evidence

ORD record
ord-4858870967fe4189a60da34c0b585ad0
Source dataset
uspto-grants-2011_10
Patent number
US08044063B2

Linked notes

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