Ethyl Acetate → HCID 67195451, compound

HRID 1259371Notes

Reaction equation

HRID 1259371 reaction equation
[CH2:1]([C:4]1([S:7](Cl)(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[C:11]([O:15][C:16]([N:18]1[C:22]2=[C:23]([NH2:38])[C:24]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][C:31]=3[F:37])=[C:25]([CH3:28])[C:26](=[O:27])[N:21]2[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(OC(=O)C)C>N1C=CC=CC=1>[C:11]([O:15][C:16]([N:18]1[C:22]2=[C:23]([NH:38][S:7]([C:4]3([CH2:1][CH:2]=[CH2:3])[CH2:6][CH2:5]3)(=[O:9])=[O:8])[C:24]([NH:29][C:30]3[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][C:31]=3[F:37])=[C:25]([CH3:28])[C:26](=[O:27])[N:21]2[CH2:20][CH2:19]1)=[O:17])([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 441819591-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chlorideHCID 67194720HCID 67194720, compound

Product 1

HCID 67195451HCID 67195451, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Allyl-cyclopropanesulfonyl chloride (121 mg, 0.001 mol) was added to a stirred solution of 8-amino-7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester (150 mg, 0.0003 mol) in pyridine (3 mL). The resulting mixture was stirred at room temperature for 12 hours. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was concentrated and partitioned between ethylacetate and water. The organic layer concentrated to afford the crude product. Purification by column chromatography on silica gel (60% ethylacetate in hexane) afforded 120 mg of the product (60.6% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethylacetate and water
  3. concentrationThe organic layer concentrated
  4. customto afford the crude product
  5. customPurification by column chromatography on silica gel (60% ethylacetate in hexane)

Sources & evidence

ORD record
ord-f4e7f38d457c4fddb2c5e459240cbdc7
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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