(Diethylamino)sulfur trifluoride → HCID 25261471, compound

HRID 1517341Notes

Reaction equation

HRID 1517341 reaction equation
C(N(S(F)(F)[F:7])CC)C.O[CH2:11][CH2:12][S:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[N:30]=[CH:29][N:28]=[C:27]([O:31][CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]3)[CH:26]=1)[CH2:20][CH2:19]2)(=[O:15])=[O:14].C(=O)(O)[O-].[Na+]>ClCCl>[F:7][CH2:11][CH2:12][S:13]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[N:30]=[CH:29][N:28]=[C:27]([O:31][CH:32]3[CH2:37][CH2:36][N:35]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][CH2:33]3)[CH:26]=1)[CH2:20][CH2:19]2)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 68561425HCID 68561425, compound

Product 1

HCID 25261471HCID 25261471, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

(Diethylamino)sulfur trifluoride (DAST, 34 μL, 0.260 mmol) was added at −78° C. to a dichloromethane (5 mL) solution of the tert-butyl 4-[(6-{5-[(2-hydroxyethyl)sulfonyl]indolin-1-yl}pyrimidin-4-yl)oxy]piperidine-1-carboxylate (43.1 mg, 0.0855 mmol) produced in Example 84, and the mixture was stirred at −78° C. for 1 hour and further stirred for 30 minutes with heating to 0° C. To the reaction solution, a saturated aqueous solution of sodium bicarbonate was added, followed by extraction with ethyl acetate three times. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-7:3, V/V) to obtain the title compound as white foam (17.0 mg, yield: 39%).

Workup

  1. stirringfurther stirred for 30 minutes
  2. temperaturewith heating to 0° C
  3. extractionfollowed by extraction with ethyl acetate three times
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-7:3, V/V)

Sources & evidence

ORD record
ord-f0b451f1b5d04fef8c6426fcfc89daea
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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