Trifluoroacetic acid → HCID 52914055, compound

HRID 1852405Notes

Reaction equation

HRID 1852405 reaction equation
[CH:1]1([S:4]([NH:7][C:8]2[C:33]([NH:34][C:35]3[CH:40]=[CH:39][C:38]([I:41])=[CH:37][C:36]=3[F:42])=[CH:32][C:31]([F:43])=[CH:30][C:9]=2[O:10][C:11]2[CH:12]=[C:13]([CH:27]=[CH:28][CH:29]=2)[CH2:14][NH:15][S:16]([NH:19]C(=O)OC(C)(C)C)(=[O:18])=[O:17])(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:43][C:31]1[CH:30]=[C:9]([O:10][C:11]2[CH:29]=[CH:28][CH:27]=[C:13]([CH2:14][NH:15][S:16](=[O:18])(=[O:17])[NH2:19])[CH:12]=2)[C:8]([NH:7][S:4]([CH:1]2[CH2:2][CH2:3]2)(=[O:5])=[O:6])=[C:33]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([I:41])=[CH:37][C:36]=2[F:42])[CH:32]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68360933HCID 68360933, compound2×

Product 1

HCID 52914055HCID 52914055, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

814 mg of tert-butyl [(3-{2-[(cyclopropylsulfonyl)amino]-5-fluoro-3-[(2-fluoro-4-iodophenyl)amino]phenoxy}benzyl)sulfamoyl]carbamate (Intermediate 18A; 1.08 mmol, 1 eq.) were dissolved in 30 mL DCM and 1.67 mL TFA were added. The reaction mixture was stirred at rt overnight. The reaction mixture was partitioned between saturated aq. sodium bicarbonate solution and dichloromethane. The pH was adjusted to pH=8 with aq. 2N sodium hydroxide solution. The layers were separated and the aqueouse layer reextracted twice with dichloromethane. The combined organic layers were washed once with brine, filtered and concentrated in vacuo. The crude product was purified by preparative HPLC providing 322 mg of the desired product (46% yield).

Workup

  1. customThe reaction mixture was partitioned between saturated aq. sodium bicarbonate solution and dichloromethane
  2. customThe layers were separated
  3. washThe combined organic layers were washed once with brine
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-c0e42521c8a3486aaecda34675bf948d
Source dataset
uspto-grants-2015_02
Patent number
US08962606B2

Reaction notes

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