Methoxyacetyl chloride → HCID 9827561, compound

HRID 1354176Notes

Reaction equation

HRID 1354176 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:31][O:32][CH2:33][C:34](Cl)=[O:35]>C1COCC1.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([NH:30][C:34](=[O:35])[CH2:33][O:32][CH3:31])(=[O:29])=[O:28])=[CH:23][CH:22]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:17])([F:18])[F:19])=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 9845828HCID 9845828, compound

Product 1

HCID 9827561HCID 9827561, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[2-(3-fluoro-phenyl)-6-trifluoromethyl-pyrazolo[1,5-a]pyridin-3-yl]-benzenesulfonamide (0.15 g 0.35 mmol) in dry THF (3 ml) was added N,N-(diisopropyl)aminomethylpolystyrene (Argonaut Technologies) (0.25 g 0.9 mmol), 4-dimethylaminopyridine (Aldrich) (0.03 g 0.25 mmol) and methoxyacetyl chloride (Aldrich) (0.09 g 0.8 mmol) and the mixture was shaken at room temperature for 18 hr. Tris-(2-aminoethyl)amine polystyrene (Argonaut Technologies) (0.5 g 1.7 mmol) was added and shaking continued for 6 hr. The resins were filtered, washed with dichloromethane (5 ml) and the solvents were removed. The residue was purified by SPE chromatography eluting with cyclohexane:ethyl acetate (5:1 then 2:1) to give the title compound as a white solid. (0.07 g, 40%).

Workup

  1. stirringshaking
  2. waitcontinued for 6 hr
  3. filtrationThe resins were filtered
  4. washwashed with dichloromethane (5 ml)
  5. customthe solvents were removed
  6. customThe residue was purified by SPE chromatography
  7. washeluting with cyclohexane:ethyl acetate (5:1

Sources & evidence

ORD record
ord-5d91734ef1e64f07a65d7b39c60456f9
Source dataset
uspto-grants-2007_05
Patent number
US07223772B1

Reaction notes

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