(Diethylamino)sulfur trifluoride → HCID 9945894, compound

HRID 2184408Notes

Reaction equation

HRID 2184408 reaction equation
O[C:2]1([C:14]2[CH:23]=[CH:22][C:17]([O:18][CH2:19][C:20]#[N:21])=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].CCN(S(F)(F)[F:30])CC>>[F:30][C:2]1([C:14]2[CH:23]=[CH:22][C:17]([O:18][CH2:19][C:20]#[N:21])=[CH:16][CH:15]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[NH:7][S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 22476595HCID 22476595, compound

Product 1

HCID 9945894HCID 9945894, compound

Procedure

The title compound was prepared in a manner analogous to the procedure set forth in example 54 from 2-[4-(1-hydroxy-2-{[(methylethyl)sulfonyl]amino}cyclopentyl)phenoxy]ethanenitrile (90 mg, 0.27 mmol) and DAST (0.01 mL) to yield the title compound (95 mg) as an oil. This material was purified by silica gel chromatography employing the Chromatotron® and using a 1000 micron rotor while eluting with a solvent methylene chloride/ethyl acetate 19:1 to yield the title compound (80 mg, 87%) as an oil. Ion Spray M.S. 339.1 (M*−1) Calculated for C16H21N2O3SF: Theory: C, 56.45; H, 6.22; N, 8.23. Found: C, 56.18; H, 6.06; N, 8.13.

Workup

  1. customThe title compound was prepared in a manner analogous to the procedure

Sources & evidence

ORD record
ord-1c4a683a14b640da8f6c335dacae8df3
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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