(Diethylamino)sulfur trifluoride → HCID 10252738, compound

HRID 2108871Notes

Reaction equation

HRID 2108871 reaction equation
O[CH2:2][C:3]1[O:4][CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][S:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([C:27]([F:30])([F:29])[F:28])=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[C:7](=[O:9])[CH:8]=1.C(N(S(F)(F)[F:37])CC)C>ClCCl>[F:28][C:27]([F:30])([F:29])[C:23]1[CH:22]=[C:21]2[C:26]([C:17]([S:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:6]3[C:7](=[O:9])[CH:8]=[C:3]([CH2:2][F:37])[O:4][CH:5]=3)=[CH:18][CH:19]=[N:20]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 10433304HCID 10433304, compound

Product 1

HCID 10252738HCID 10252738, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Hydroxymethyl-5-[5-(7-trifluoromethyl-quinolin-4-ylsulfanyl)-pentyloxy]-pyran-4-one EHT 5909 (100 mg, 0.23 mmol) was dissolved in dichloromethane (5 mL). The mixture was stirred at 0° C. for 15 min. Diethylaminosulfur trifluoride (DAST, 33 μL, 0.25 mmol) was added via syringe. The mixture was stirred at room temperature for 10 min. The solution was evaporated. The crude product was purified by flash chromatography on silica using as eluent CH2Cl2:MeOH=99:01. 5-(5-(7-(Trifluoromethyl)quinolin-4-ylthio)pentyloxy)-2-(fluoromethyl)-4H-pyran-4-one EHT 8817 was obtained (48 mg, 35% yield) as a white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 10 min
  2. customThe solution was evaporated
  3. customThe crude product was purified by flash chromatography on silica using as eluent CH2Cl2

Sources & evidence

ORD record
ord-bfd492014535490dbbc0d8a544d8cc96
Source dataset
uspto-grants-2009_04
Patent number
US07514432B2

Reaction notes

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