Trifluoroacetic acid → HCID 57624911, compound

HRID 881646Notes

Reaction equation

HRID 881646 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=3[F:30])[C:16]=2[C:31](=[O:33])[NH2:32])[CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH2:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=2[F:30])[C:16]=1[C:31]([NH2:32])=[O:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44469439HCID 44469439, compound

Product 1

HCID 57624911HCID 57624911, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In analogy to GP 4, 163 mg of {3-[2-Carbamoyl-5-fluoro-3-(2-fluoro-4-iodo-phenylamino)-phenoxy]-phenyl}-carbamic acid tert-butyl ester (0.28 mmol) were suspended in dichloromethane, 0.29 ml of TFA (3.78 mmol, 13 eq.) were added and the mixture was stirred at rt for 4 h. The reaction mixture was concentrated, redissolved in dichloromethane and sodium hydroxide solution (1M, aq.) was added. After phase separation the organic phase was concentrated to afford 129 mg (96%, 0.27 mmol) of the desired product, which required no further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionredissolved in dichloromethane
  3. additionsodium hydroxide solution (1M, aq.) was added
  4. customAfter phase separation the organic phase
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-edc21b3fac574ddcb72c6c280899379f
Source dataset
uspto-grants-2015_03
Patent number
US08993630B2

Reaction notes

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