Ethyl Acetate → HCID 67195013, compound

HRID 1259363Notes

Reaction equation

HRID 1259363 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]([Br:22])=[CH:18][C:17]=2[F:23])=[C:13]([CH3:24])[C:12](=[O:25])[N:11]2[CH2:26][CH2:27][N:28]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:10]=12.C(OC(=O)C)C>N1C=CC=CC=1>[CH2:29]([N:28]1[C:10]2=[C:9]([NH:8][S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])[C:14]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=3[F:23])=[C:13]([CH3:24])[C:12](=[O:25])[N:11]2[CH2:26][CH2:27]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2760919Cyclopropanesulfonyl chlorideHCID 67192849HCID 67192849, compound

Product 1

HCID 67195013HCID 67195013, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cyclopropanesulfonyl chloride (254 mg, 0.0002 mol) was added to a stirred solution of 8-amino-1-benzyl-7-(4-bromo-2-fluoro-phenylamino)-6-methyl-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one (400 mg, 0.001 mol) in pyridine (4 mL). The resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was monitored by TLC (100% ethylacetate). The reaction mixture was concentrated and partitioned between ethylacetate and water. The organic layer was concentrated to afford the crude product. Purification by column chromatography on silica gel (80% ethylacetate in hexane), followed by preparative HPLC afforded 30 mg of the product (6% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethylacetate and water
  3. concentrationThe organic layer was concentrated
  4. customto afford the crude product
  5. customPurification by column chromatography on silica gel (80% ethylacetate in hexane)

Sources & evidence

ORD record
ord-b69b531d04b147f1b0997b26d5c2f266
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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