Pyridine → HCID 11199101, compound
Reaction equation
[F:1][C:2]([F:13])([F:12])[CH:3]([C:8]([F:11])([F:10])[F:9])[CH:4]([NH2:7])[CH2:5][OH:6].N1C=CC=CC=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[F:1][C:2]([F:12])([F:13])[CH:3]([C:8]([F:9])([F:10])[F:11])[CH:4]([NH:7][S:25]([C:21]1[S:20][CH:24]=[CH:23][CH:22]=1)(=[O:27])=[O:26])[CH2:5][OH:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 3,3,3-trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propylamine (prepared according to the method of Example 28, Part A, 105 mg, 0.5 mmol) in CH2Cl2 (1 mL) was added pyridine (100 μL) and 2-thiophenesulfonyl chloride (90.5 mg, 0.5 mmol) in CH2Cl2 (1 mL). The solution was stirred for about 8 to about 16 h at 25° C. and then concentrated. EtOAc (1 mL) was added and the solution was washed with 1M HCl (1 mL), brine (1 mL), dried over Na2SO4 and concentrated. The crude solid was purified by the Biotage Flash™ 12 chromatography system, eluting with EtOAc/hexanes (2:3), to give thiophene-2-sulfonic acid (3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-amide (26.5 mg) as a white solid.
Workup
- concentrationconcentrated
- additionEtOAc (1 mL) was added
- washthe solution was washed with 1M HCl (1 mL), brine (1 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe crude solid was purified by the Biotage Flash™ 12 chromatography system
- washeluting with EtOAc/hexanes (2:3)
Sources & evidence
- ORD record
- ord-1f1bae28c4c0436488bb96ab08c64e9e
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07300951B2
Reaction notes
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