Ethyl Acetate → Cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide

HRID 1259387Notes

Reaction equation

HRID 1259387 reaction equation
[CH:1]1([S:4](Cl)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[NH2:8][C:9]1[C:14]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])=[C:13]([CH3:24])[C:12](=[O:25])[N:11]2[CH2:26][CH2:27][O:28][C:10]=12.C(OC(=O)C)C>N1C=CC=CC=1>[F:23][C:17]1[CH:18]=[C:19]([I:22])[CH:20]=[CH:21][C:16]=1[NH:15][C:14]1[C:9]([NH:8][S:4]([CH:1]2[CH2:3][CH2:2]2)(=[O:6])=[O:5])=[C:10]2[O:28][CH2:27][CH2:26][N:11]2[C:12](=[O:25])[C:13]=1[CH3:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2760919Cyclopropanesulfonyl chlorideHCID 58380528HCID 58380528, compound

Product 1

HCID 52934091Cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amideYield 3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cyclopropane sulfonyl chloride (50 mg, 0.35 mmol) was added to a solution of 8-amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-2,3-dihydro-oxazolo[3,2-a]pyridin-5-one (I-7f: 80 mg, 0.199 mmol) in dry pyridine (1 mL) at 0° C. The resulting mixture was stirred at room temperature for 1 hour. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was partitioned between ethylacetate and water. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1.5% MeOH in DCM) afforded 3 mg of the product (3% yield).

Workup

  1. customThe reaction mixture was partitioned between ethylacetate and water
  2. washThe organic layer was washed with water, brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (1.5% MeOH in DCM)

Sources & evidence

ORD record
ord-e61906dcf3864c5d898a47cd3fcd4ac7
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

Loading…