3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole → HCID 86650728, compound

HRID 336979Notes

Reaction equation

HRID 336979 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[N:12]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[C:11](=[O:28])[N:10]2[CH3:29])=[C:5]([SH:30])[CH:4]=1)#[N:2].CC1(C)C2C=CC=CC=2I([C:41]([F:44])([F:43])[F:42])O1>ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[N:12]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=3)[C:11](=[O:28])[N:10]2[CH3:29])=[C:5]([S:30][C:41]([F:44])([F:43])[F:42])[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 160435723,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxoleHCID 66602208HCID 66602208, compound

Product 1

HCID 86650728HCID 86650728, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon, (4S)-4-(4-cyano-2-sulfanylphenyl)-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (45 mg, purity 50%, 53 μmol) was dissolved in dichloromethane (1 ml). At −78° C., 3,3-dimethyl-1-(trifluoromethyl)-1,3-dihydro-1λ3,2-benziodoxole (26 mg, 79 μmol; 1.5 eq.) was added, and the mixture was stirred for 2 h. The reaction solution was then concentrated under reduced pressure, and the residue was purified by preparative HPLC (Kromasil C18 column, 20×50 mm; mobile phase: acetonitrile/water+0.1% TFA). After lyophilization, the title compound was obtained as a solid (11.4 mg, 44% of theory).

Workup

  1. concentrationThe reaction solution was then concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC (Kromasil C18 column, 20×50 mm; mobile phase: acetonitrile/water+0.1% TFA)

Sources & evidence

ORD record
ord-b5229bd10a494819855e870fd2fe6b8e
Source dataset
uspto-grants-2014_11
Patent number
US08889700B2

Reaction notes

Loading…