1,2-Dichloroethane → HCID 71542366, compound

HRID 1776609Notes

Reaction equation

HRID 1776609 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[OH:10].[CH3:28][S:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]([CH2:41][C:42](O)=[O:43])[S:37]([CH3:40])(=[O:39])=[O:38])=[CH:32][CH:31]=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:27])[CH:5]=[C:6]([Cl:26])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH:12]=1)[O:10][C:42](=[O:43])[CH2:41][N:36]([C:33]1[CH:34]=[CH:35][C:30]([S:29][CH3:28])=[CH:31][CH:32]=1)[S:37]([CH3:40])(=[O:38])=[O:39]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 71092687HCID 71092687, compoundHCID 89459986HCID 89459986, compound

Product 1

HCID 71542366HCID 71542366, compoundYield 41.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide 30 mg, 0.071 mmol), 2-(N-(4-(methylthio)phenyl)methyl-sulfonamido)acetic acid (39.3 mg, 0.143 mmol), DMAP (17.44 mg, 0.143 mmol), and EDC (41.1 mg, 0.214 mmol) were dissolved in DMF (1.5 ml). The reaction was stirred at RT overnight to achieve completion. The reaction mixture was diluted with water and extracted with EtOAc. The organic phase was washed with HCl 1N, Na2CO3 sat. sol. and brine, dried over Na2SO4 and concentrated under vacuum. The crude product was purified by Preparative reverse-phase HPLC to give (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(N-(4-(methylthio)phenyl)methylsulfonamido)-acetoxy)ethyl)pyridine 1-oxide (20 mg, 41.3% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with HCl 1N, Na2CO3 sat. sol. and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe crude product was purified by Preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-0dbd212ebd0644b18e8d2065a41ce669
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…