(Diethylamino)sulfur trifluoride → HCID 11655097, compound

HRID 386512Notes

Reaction equation

HRID 386512 reaction equation
[CH2:1]1[N:6]([CH2:7][C:8]([NH:10][CH:11]2[CH:16]3[CH2:17][C:18]4(O)[CH2:20][CH:12]2[CH2:13][CH:14]([CH2:19]4)[CH2:15]3)=[O:9])[CH2:5][CH2:4][N:3]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=2)[CH2:2]1.C(N(S(F)(F)[F:38])CC)C>C(Cl)Cl>[CH2:1]1[N:6]([CH2:7][C:8]([NH:10][CH:11]2[CH:16]3[CH2:17][C:18]4([F:38])[CH2:20][CH:12]2[CH2:13][CH:14]([CH2:19]4)[CH2:15]3)=[O:9])[CH2:5][CH2:4][N:3]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=2)[CH2:2]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 11495851HCID 11495851, compound

Product 1

HCID 11655097HCID 11655097, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[(E)-5-hydroxy-2-adamantyl]-2-{4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}acetamide (66 mg, 0.15 mmoles) from Example 2 in DCM (0.5 mL) was cooled to −78° C., treated with (diethylamino)sulfur trifluoride (DAST) (0.020 mL, 0.16 mmoles) and slowly warmed to room temperature over 6 hours. The mixture was quenched with aqueous saturated sodium bicarbonate (0.1 mL), filtered through a Celite cartridge and purified (silica gel, 10-15% acetone in hexane) to provide the title compound as a white solid.

Workup

  1. customThe mixture was quenched with aqueous saturated sodium bicarbonate (0.1 mL)
  2. filtrationfiltered through a Celite cartridge
  3. custompurified (silica gel, 10-15% acetone in hexane)

Sources & evidence

ORD record
ord-8f9b3d621e394f629c4dddef127c083f
Source dataset
uspto-grants-2013_02
Patent number
US08372841B2

Reaction notes

Loading…