p-Toluenesulfonic acid → HCID 67253227, compound

HRID 1914877Notes

Reaction equation

HRID 1914877 reaction equation
[NH2:1][C:2]1[C:19]([F:20])=[C:18]([F:21])[C:5]2[N:6]([C:10]3[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=3[F:17])[C:7](=[O:9])[NH:8][C:4]=2[C:3]=1[OH:22].[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C(OCC)(OCC)OCC.CCCCCC>[F:20][C:19]1[C:2]2[N:1]=[CH:23][O:22][C:3]=2[C:4]2[NH:8][C:7](=[O:9])[N:6]([C:10]3[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=3[F:17])[C:5]=2[C:18]=1[F:21]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 68313323HCID 68313323, compound

Product 1

HCID 67253227HCID 67253227, compoundYield 535.3%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 31214Ethyl orthoformateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-amino-6,7-difluoro-1-(2-fluoro-4-iodo-phenyl)-4-hydroxy-1,3-dihydro-benzoimidazol-2-one (I-13a: 550 mg, 1.3 mmol) in triethyl orthoformate (5 mL) and p-toluene sulfonic acid (20 mg, 0.13 mmol) were taken in a flask and the flask was heated to reflux at 120° C. for 30 minutes. The reaction was monitored by TLC (70% ethyl acetate in hexane). The reaction mixture was concentrated under reduced pressure and the concentrate was triturated with diethyl ether and filtered. The residue was washed with diethyl ether and dried under reduced pressure to afford 300 mg of the product (54.5% yield). H1NMR (DMSO-d6, 300 MHz): δ 12.50 (s, 1H), 8.87 (s, 1H), 7.97 (dd, 1H), 7.78 (d, 1H), 7.50 (t, 1H). LCMS: 92.2%, m/z=431.9 (M+1).

Workup

  1. customwere taken in a flask
  2. temperaturethe flask was heated
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe concentrate was triturated with diethyl ether
  5. filtrationfiltered
  6. washThe residue was washed with diethyl ether
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-66c732bbf0ae4818aeb2a84d6907bf44
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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