(Diethylamino)sulfur trifluoride → HCID 11655097, compound

HRID 2276930Notes

Reaction equation

HRID 2276930 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.CCN(S(F)(F)[F:38])CC>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—[(Z)-5-hydroxy-2-adamantyl]-2-{4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}acetamide (66 mg, 0.15 mmoles) from Example 1D in DCM (0.5 mL) was cooled to −78° C., treated with DAST (0.020 mL, 0.16 mmoles) and slowly warmed to room temperature for 6 hours. The mixture was quenched by the addition of 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. 1H NMR (300 MHz, CDCl3) δ 8.42 (s, 1H), 7.67 (m, 2H), 6.67 (d, J=9.1 Hz, 1H), 3.97 (s, 1H), 3.7 (s, 4H), 3.1 (s, 2H), 2.68 (s, 4H), 2.29-2.24 (m, 3H), 1.91-1.7 (m, 10H); MS (APCI+) m/z 441 (M+H)+.

Workup

  1. customThe mixture was quenched by the addition of 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-df042d68c9b34a6aae0d1291b7f509d5
Source dataset
uspto-grants-2015_09
Patent number
US09133145B2

Reaction notes

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