Trifluoroacetic acid → HCID 67073703, compound

HRID 1852396Notes

Reaction equation

HRID 1852396 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[NH:31][S:32]([CH:35]2[CH2:37][CH2:36]2)(=[O:34])=[O:33])[CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[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[NH:31][S:32]([CH:35]1[CH2:36][CH2:37]1)(=[O:33])=[O:34]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 68360916HCID 68360916, compound

Product 1

HCID 67073703HCID 67073703, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.19 g of tert-butyl(3-{2-[(cyclopropylsulfonyl)amino]-5-fluoro-3-[(2-fluoro-4-iodophenyl)amino]phenoxy}phenyl)carbamate (1.8 mmol, 1 eq.) were dissolved in 15 mL DCM, treated with 2 mL TFA and stirred at rt for 6 h. The reaction mixture was cooled to 0° C. and adjusted with 1N Sodium hydroxide to pH 10. The layers were separated, the aqueous layer was reextracted with DCM. The combined organic layers were dried, filtered and concentrated in vacuo to yield 776 mg of the crude product (77% yield), which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customThe layers were separated
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9f86bc4f46942ddaa06c7bded39c65b
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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