Water → HCID 56592070, compound

HRID 1616081Notes

Reaction equation

HRID 1616081 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([S:9]([CH3:12])(=[O:11])=[O:10])[CH:6]=[CH:5][C:4]=1[NH:13][C:14]1[C:15]2[O:22][CH:21]=[C:20]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[C:16]=2[N:17]=[CH:18][N:19]=1.[F:29][C:30]([F:46])([F:45])[C:31]1[CH:32]=[C:33]([S:41](Cl)(=[O:43])=[O:42])[CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1.O>N1C=CC=CC=1.C(Cl)Cl>[F:40][C:37]([F:38])([F:39])[C:35]1[CH:34]=[C:33]([S:41]([N:26]2[CH2:27][CH2:28][CH:23]([C:20]3[C:16]4[N:17]=[CH:18][N:19]=[C:14]([NH:13][C:4]5[CH:5]=[CH:6][C:7]([S:9]([CH3:12])(=[O:10])=[O:11])=[CH:8][C:3]=5[F:2])[C:15]=4[O:22][CH:21]=3)[CH2:24][CH2:25]2)(=[O:42])=[O:43])[CH:32]=[C:31]([C:30]([F:46])([F:45])[F:29])[CH:36]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5209453,5-Bis(trifluoromethyl)benzenesulphonyl chlorideHCID 86681873HCID 86681873, compound

Product 1

HCID 56592070HCID 56592070, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

N-[2-Fluoro-4-(methylsulfonyl)phenyl]-7-(piperidin-4-yl)furo[3,2-d]pyrimidine-4-amine hydrochloride (10 mg, 0.023 mmol) was dissolved in pyridine (0.1 mL), a solution of 3,5-bis(trifluoromethyl)benzene-1-sulfonyl chloride (14 mg, 0.046 mmol) in anhydrous methylene chloride (0.4 mL) was added under ice-cooling, followed by stirring at room temperature for 1 hour and 45 minutes. Water was added to the reaction liquid, followed by extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and the obtained residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=50:1) to give the titled compound (6.3 mg, 41%) as a white solid.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customthe obtained residue was purified by silica gel preparative thin layer chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-7f506eca57204ad88f3414441bb0fe53
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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