HCID 12150103, compound → HCID 12150104, compound

HRID 1884608Notes

Reaction equation

HRID 1884608 reaction equation
C([O:5][C:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[C:26]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:25]=[C:24]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[C:23]=2[O:37][CH3:38])=[O:20])=[CH:10][CH:9]=1)=[O:7])(C)(C)C>[Au].C(O)(C(F)(F)F)=O>[C:28]([C:26]1[CH:25]=[C:24]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[C:23]([O:37][CH3:38])=[C:22]([NH:21][C:19](=[O:20])[NH:18][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([C:6]([OH:7])=[O:5])=[CH:9][CH:10]=2)[CH:27]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 1

HCID 12150103HCID 12150103, compound

Product 1

HCID 12150104HCID 12150104, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

To a 0° C. solution of 10 mL of TFA was added 878 mg (1.9 mmol) of 4-[3-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-ureido]-naphthalene-1-carboxylic acid tert-butyl ester. The clear, light gold reaction was allowed to warm to room temperature, and kept there for 1 h. After this time, the reaction was concentrated in vacuo, and then diluted with toluene. The toluene was then removed in vacuo and the pale white solid was triturated with ether to provide 682 mg (89%) of the title compound.

Workup

  1. concentrationAfter this time, the reaction was concentrated in vacuo
  2. additiondiluted with toluene
  3. customThe toluene was then removed in vacuo
  4. customthe pale white solid was triturated with ether

Sources & evidence

ORD record
ord-a74cbf86aec6495b880a69bcde8de4c6
Source dataset
uspto-grants-2004_07
Patent number
US06765009B2

Reaction notes

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