Methoxyacetyl chloride → HCID 52934277, compound

HRID 1043015Notes

Reaction equation

HRID 1043015 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:26][CH3:27])=[C:5]([CH3:28])[O:4][N:3]=1.[CH3:29][O:30][CH2:31][C:32](Cl)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:27][O:26][C:8]1[C:7]([C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:28])=[CH:16][C:15]2[N:14]=[CH:13][C:12]3[N:17]=[C:32]([CH2:31][O:30][CH3:29])[N:18]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[C:11]=3[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 96623Methoxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 672071317-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-N4-(2-pyridinylmethyl)-3,4-quinolinediamine2×

Product 1

HCID 52934277HCID 52934277, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-N4-(pyridin-2-ylmethyl)quinoline-3,4-diamine (for a preparation see Intermediate 63, 500 mg) was dissolved in DCM (20 ml) and the reaction mixture was cooled to 0° C. 2-Methoxyacetyl chloride (1.1 eq) was added dropwise and the reaction mixture was stirred at room temperature for 30 min. The mixture was hydrolysed using a solution of sodium hydrogen carbonate and extracted with DCM. The organic was dried over Na2SO4, filtered and concentrated to dryness. The obtained residue was dissolved in acetic acid (5 ml) and the reaction mixture was heated to 130° C. for 16 h. The reaction mixture was treated with sodium hydroxide (1M) and extracted with DCM. The organic was dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel, eluting with DCM/methanol (95:5). The resulting compound was recrystallised from acetonitrile and dried under vacuum to give 4-(8-methoxy-2-(methoxymethyl)-1-(pyridin-2-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole (50 mg) as a cream-coloured powder.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. dissolutionThe obtained residue was dissolved in acetic acid (5 ml)
  6. temperaturethe reaction mixture was heated to 130° C. for 16 h
  7. additionThe reaction mixture was treated with sodium hydroxide (1M)
  8. extractionextracted with DCM
  9. dry with materialThe organic was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated to dryness
  12. customThe residue was purified by chromatography on silica gel
  13. washeluting with DCM/methanol (95:5)
  14. customThe resulting compound was recrystallised from acetonitrile
  15. customdried under vacuum

Sources & evidence

ORD record
ord-f93046ae0dbf4c04929e1f8dbad45c49
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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