Water → HCID 56592071, compound

HRID 1616082Notes

Reaction equation

HRID 1616082 reaction equation
[CH:1]1([S:4](Cl)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl.[F:16][C:17]1[CH:22]=[C:21]([S:23]([CH3:26])(=[O:25])=[O:24])[CH:20]=[CH:19][C:18]=1[NH:27][C:28]1[C:29]2[O:36][CH:35]=[C:34]([CH:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)[C:30]=2[N:31]=[CH:32][N:33]=1.O>C(#N)C>[CH:1]1([S:4]([N:40]2[CH2:39][CH2:38][CH:37]([C:34]3[C:30]4[N:31]=[CH:32][N:33]=[C:28]([NH:27][C:18]5[CH:19]=[CH:20][C:21]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:22][C:17]=5[F:16])[C:29]=4[O:36][CH:35]=3)[CH2:42][CH2:41]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 86681873HCID 86681873, compound

Product 1

HCID 56592071HCID 56592071, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of cyclopropanesulfonyl chloride (4 mg, 0.028 mmol) in anhydrous acetonitrile (0.2 mL), and triethylamine (10 μL, 0.069 mmol) were added to N-[2-fluoro-4-(methylsulfonyl)phenyl]-7-(piperidin-4-yl)furo[3,2-d]pyrimidine-4-amine hydrochloride (10 mg, 0.023 mmol) under ice-cooling, followed by stirring at room temperature for 2 hours. Water was added to the reaction liquid, followed by extraction with chloroform, and 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 (8.5 mg, 75%) as a pale yellow solid.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  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-5a7a9cb2996143bcb72c861098ce8496
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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