(Diethylamino)sulfur trifluoride → HCID 66832030, compound

HRID 1918765Notes

Reaction equation

HRID 1918765 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][NH:22][C:23]([C:25]1[CH:29]=[C:28]([CH:30]([C:32]2[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=2[F:39])O)[O:27][N:26]=1)=[O:24]>ClCCl>[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][CH2:21][NH:22][C:23]([C:25]1[CH:29]=[C:28]([CH:30]([C:32]2[CH:37]=[C:36]([F:38])[CH:35]=[CH:34][C:33]=2[F:39])[F:7])[O:27][N:26]=1)=[O:24]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 49868776HCID 49868776, compound

Product 1

HCID 66832030HCID 66832030, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylaminosulfur trifluoride (0.033 mL; 0.197 mmol) was added to a solution of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-((2,5-difluorophenyl)(hydroxy)methyl)isoxazole-3-carboxamide (0.074 g; 0.171 mmol) in dichloromethane (5 mL) at −78° C., the resulting mixture was stirred at room temperature for 3 hours, cooled to 0° C. and quenched with water. The layers were separated, the aqueous layer was extracted with dichloromethane. The organic layers rejoined were dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) and by preparative HPLC method 2 to yield 0.005 g (7%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-((2,5-difluorophenyl)fluoromethyl)isoxazole-3-carboxamide as a white solid.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. dry with materialThe organic layers rejoined were dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) and by preparative HPLC method 2

Sources & evidence

ORD record
ord-36533c1e7ca6432daf599baf260b8425
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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