(Diethylamino)sulfur trifluoride → HCID 71765090, compound

HRID 2272976Notes

Reaction equation

HRID 2272976 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:7]([C:11]3[CH:16]=[CH:15][C:14]([C:17](O)([CH3:19])[CH3:18])=[CH:13][CH:12]=3)=[CH:6][N:5]2[CH:21]=1.C(N(S(F)(F)[F:28])CC)C>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][C:7]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:28])([CH3:19])[CH3:18])=[CH:13][CH:12]=3)=[CH:6][N:5]2[CH:21]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 71765087HCID 71765087, compound

Product 1

HCID 71765090HCID 71765090, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A suspension of 57.3 mg (0.20 mmol) 7-fluoro-3-[4-(1-hydroxy-1-methyl-ethyl)phenyl]-2H-pyrrolo[1,2-a]pyrazin-1-one in 0.5 ml dichloromethane is cooled to −78° C. Then 105 μl (0.80 mmol) diethylaminosulfurtrifluoride are added. The reaction mixture is allowed to reach room temperature over 30 minutes. The reaction mixture is evaporated and the residue is treated with water and saturated sodium hydrogen carbonate solution. The solids are filtered off and chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 7-fluoro-3-[4-(1-fluoro-1-methyl-ethyl)-phenyl]-2H-pyrrolo[1,2-a]pyrazin-1-one as white powder; HPLC/MS 2.60 min (B), [M+H] 289; 1H NMR (400 MHz, DMSO-d6) δ [ppm]11.01 (s, 1H), 7.70-7.63 (m, 3H), 7.53-7.44 (m, 3H), 6.76 (d, J=1.9 Hz, 1H), 1.67 (d, J=22.2 Hz, 6H).

Workup

  1. customThe reaction mixture is evaporated
  2. additionthe residue is treated with water and saturated sodium hydrogen carbonate solution
  3. filtrationThe solids are filtered off
  4. customchromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-97ffef3b8b9a4decb069d76d891e4398
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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