Pyridine → HCID 11417003, compound

HRID 2266920Notes

Reaction equation

HRID 2266920 reaction equation
[F:1][C:2]([F:13])([F:12])[CH:3]([C:8]([F:11])([F:10])[F:9])[C@H:4]([NH2:7])[CH2:5][OH:6].N1C=CC=CC=1.[S:20]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21]1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.CCOC(C)=O>[F:1][C:2]([F:12])([F:13])[CH:3]([C:8]([F:9])([F:10])[F:11])[C@H:4]([NH:7][S:25]([C:22]1[CH:23]=[CH:24][S:20][CH:21]=1)(=[O:27])=[O:26])[CH2:5][OH:6]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 2776378Thiophene-3-sulfonyl ChlorideHCID 25022953HCID 25022953, compound

Product 1

HCID 11417003HCID 11417003, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (1S)-3,3,3-trifluoro-2-(trifluoromethyl)-1-(hydroxymethyl)propylamine (prepared according to the method of Example 13, 0.100 g, 0.4 mmol) in CH2Cl2 (1 mL) was stirred under nitrogen at 25° C. Pyridine (0.097 mL, 1.2 mmol) was added followed by 3-thiophenesulfonyl chloride (0.072 g, 0.4 mmol) in CH2Cl2 (0.5 mL), and the resulting solution stirred for 18 h at 25° C. The crude reaction mixture was loaded onto the TsOH Syntage™ samplet and after concentration was purified by the Biotage Flash™ 12 chromatography system, eluent: 30:70 EtOAc:hexanes, to obtain N-[(1S)-3,3,3-trifluoro-1-(hydroxymethyl)-2-(trifluoromethyl)propyl]thiophene-3-sulfonamide as a white solid (0.053 g, 35% yield).

Workup

  1. stirringthe resulting solution stirred for 18 h at 25° C
  2. customThe crude reaction mixture
  3. concentrationafter concentration
  4. customwas purified by the Biotage Flash™ 12 chromatography system, eluent

Sources & evidence

ORD record
ord-adab2889995a4c7887e2e70e8fa30c8b
Source dataset
uspto-grants-2010_12
Patent number
US07858658B2

Reaction notes

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