Ethyl Acetate → HCID 52934782, compound

HRID 1259364Notes

Reaction equation

HRID 1259364 reaction equation
C([N:8]1[C:12]2=[C:13]([NH:28][S:29]([CH:32]3[CH2:34][CH2:33]3)(=[O:31])=[O:30])[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)C1C=CC=CC=1.C(OC(=O)C)C>C(Cl)Cl>[Br:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:14]2[C:13]([NH:28][S:29]([CH:32]3[CH2:34][CH2:33]3)(=[O:31])=[O:30])=[C:12]3[NH:8][CH2:9][CH2:10][N:11]3[C:16](=[O:17])[C:15]=2[CH3:18])=[C:21]([F:27])[CH:22]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 67195013HCID 67195013, compound

Product 1

HCID 52934782HCID 52934782, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Borontribromide (20 mg, 0.0001 mol) was added to a stirred solution of cyclopropanesulfonic acid [1-benzyl-7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyridin-8-yl]-amide (1A: 30 mg, 0.0001 mol) in DCM (3 mL) at 0° C. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was monitored by TLC (100% ethylacetate). The reaction mixture was quenched with methanol and concentrated. The concentrate was partitioned between ethyl acetate and water. The organic layer was concentrated to afford the crude product. Purification by column chromatography on silica gel (4% methanol in DCM) afforded 7 mg of the product (28% yield).

Workup

  1. customThe reaction mixture was quenched with methanol
  2. concentrationconcentrated
  3. customThe concentrate was partitioned between ethyl acetate and water
  4. concentrationThe organic layer was concentrated
  5. customto afford the crude product
  6. customPurification by column chromatography on silica gel (4% methanol in DCM)

Sources & evidence

ORD record
ord-772258b0716e45dbb15f03dbcf7277c8
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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