Dimethyl Sulfide → HCID 53358566, compound

HRID 1807317Notes

Reaction equation

HRID 1807317 reaction equation
[Cl:1][C:2]1[C:3]([F:41])=[C:4]([C@@H:8]2[C@:12]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[F:22])([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[NH:10][C@H:9]2[C:28]([NH:30][C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37]C)=[O:36])=[CH:33][N:32]=2)=[O:29])[CH:5]=[CH:6][CH:7]=1.[Br-].[Al+3].[Br-].[Br-].CSC>C(Cl)Cl>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C@@:12]2([C:13]#[N:14])[C@H:11]([CH2:23][C:24]([CH3:26])([CH3:25])[CH3:27])[NH:10][C@@H:9]([C:28]([NH:30][C:31]3[CH:40]=[CH:39][C:34]([C:35]([OH:37])=[O:36])=[CH:33][N:32]=3)=[O:29])[C@@H:8]2[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[F:41])=[C:16]([F:22])[CH:17]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 166749BromhydrolHCID 53358817HCID 53358817, compound

Product 1

HCID 53358566HCID 53358566, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottomed flask, methyl 6-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)nicotinate (25 mg, 41.6 μmol, Eq: 1.00) was dissolved in methylene chloride (8 ml) to give a colorless solution. Aluminum bromide (66.5 mg, 249 μmol, Eq: 6) and dimethyl sulfide (25.8 mg, 30.7 μl, 416 μmol, Eq: 10) were added and the mixture was stirred at rt for overnight. The solvent was removed and the residue was suspended in 3 ml of acetonitrile, 3 ml of water was added and the mixture was extracted with ethyl acetate (3×8 ml). The extracts were combined and dried with sodium sulfate. Removal of solvent at reduced pressure gave a yellow solid, 30 mg.

Workup

  1. customto give a colorless solution
  2. customThe solvent was removed
  3. addition3 ml of water was added
  4. extractionthe mixture was extracted with ethyl acetate (3×8 ml)
  5. dry with materialdried with sodium sulfate
  6. customRemoval of solvent at reduced pressure
  7. customgave a yellow solid, 30 mg

Sources & evidence

ORD record
ord-ae877b358b154040bb20c98fe4a156dd
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

Loading…