Ethyl Acetate → HCID 60026306, compound

HRID 400668Notes

Reaction equation

HRID 400668 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:42])[C:6]([C:16]#[C:17][CH2:18][C:19]([OH:41])([C:37]([F:40])([F:39])[F:38])[CH2:20][C:21]([C:24]2[C:32]3[O:31][CH2:30][CH2:29][C:28]=3[CH:27]=[C:26]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:25]=2)([CH3:23])[CH3:22])=[C:7]([NH:9]C(=O)C(F)(F)F)[CH:8]=1)#[N:2].CN(C)C(N(C)C)=N.C(OCC)(=O)C>CS(C)=O.ClCCl>[OH:41][C:19]([C:37]([F:39])([F:40])[F:38])([CH2:20][C:21]([C:24]1[C:32]2[O:31][CH2:30][CH2:29][C:28]=2[CH:27]=[C:26]([S:33]([CH3:36])(=[O:34])=[O:35])[CH:25]=1)([CH3:22])[CH3:23])[CH2:18][C:17]1[NH:9][C:7]2[C:6]([CH:16]=1)=[C:5]([CH3:42])[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=2

Participants

6

Reactant 3

HCID 8857Ethyl Acetate2×HCID 664601,1,3,3-TetramethylguanidineHCID 86600089HCID 86600089, compound

Product 1

HCID 60026306HCID 60026306, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-{5-cyano-2-[4-hydroxy-6-(5-methanesulfonyl-2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-ynyl]-3-methylphenyl}-2,2,2-trifluoroacetamide (154 mg, 0.25 mmol) in 0.6 mL of anhydrous DMSO was heated in the presence of 1,1,3,3-tetramethylguanidine (0.094 mL, 0.75 mmol) in a microwave at 140° C. for 10 minutes. The reaction was quenched with a mixture of 1 N sulfuric acid and 10 mL of crushed ice. The resulting precipitate was filtered, washed with water, and dried. Preparative TLC chromatography (50% ethyl acetate in hexanes, followed by 15% ethyl acetate in dichloromethane) gave 23 mg of the title product as an off-white solid (18% yield).

Workup

  1. customThe reaction was quenched with a mixture of 1 N sulfuric acid and 10 mL of crushed ice
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-dac6812f74054170ace9a892b9dab524
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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