Dimethyl Sulfoxide → Trifluoroacetic acid

HRID 2214226Notes

Reaction equation

HRID 2214226 reaction equation
F[C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:34][C:35]1[CH:43]=[C:42]2[C:38]([CH:39]=[N:40][NH:41]2)=[CH:37][CH:36]=1.CS(C)=[O:46]>>[C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:46].[NH:41]1[C:42]2[C:38](=[CH:37][CH:36]=[C:35]([NH:34][C:2]3[C:7]([C:8]([NH:10][C:11]4[CH:12]=[CH:13][C:14]([C:17]([O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])([C:22]([F:25])([F:23])[F:24])[C:18]([F:20])([F:19])[F:21])=[CH:15][CH:16]=4)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=3)[CH:43]=2)[CH:39]=[N:40]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 814231H-Indazol-6-amineHCID 131725936HCID 131725936, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 10304079HCID 10304079, compound

Conditions

Temperature
120 °C

Procedure

To a suspension of 2-fluoropyridine-3-carbonyl chloride (180 mg, 0.5 mmol, Step B) and NaHCO3 (300 mg) in CH2Cl2 (5 ml), a solution of 4-{2,2,2-trifluoro-1-[2-(2-methoxy)ethoxy]-1-(trifluoromethyl)ethyl}phenylamine (95 mg) was added dropwise, and the suspension was stirred at RT for 1.5 h. Solid inorganic salts were removed via filtration. The filtrate was concentrated to afford (2-fluoro(3-pyridyl))-N-(4-{2,2,2-trifluoro-1-[2-(2-methoxyethoxy)ethoxy]-1-(trifluoromethyl)ethyl}phenyl)-carboxamide as a brown solid. (2-Fluoro(3-pyridyl))-N-(4-{2,2,2-trifluoro-1-[2-(2-methoxyethoxy)ethoxy]-1-(trifluoromethyl)ethyl}-phenyl)carboxamide (240 mg, 0.5 mmol) and 6-amino-indazole (133 mg, 1 mmol) were dissolved in DMSO (2 mL). The solution was heated to 120° C. for 8 h, then partitioned between CH2Cl2 and aqueous NaHCO3 (sat.). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified via preparative HPLC to give a yellow powder as a TFA salt of the title compound. MS: 598 (M+1). Calc'd. for C27H25F6N5O4—597.5.

Workup

  1. custompartitioned between CH2Cl2 and aqueous NaHCO3 (sat.)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-6083fee07e05412fa00ef6b520746f68
Source dataset
uspto-grants-2006_09
Patent number
US07105682B2

Reaction notes

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