N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[2-hydroxy-1-(hydroxymethyl)ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide → HCID 86619881, compound

HRID 1024910Notes

Reaction equation

HRID 1024910 reaction equation
[CH3:1][C:2]1([CH3:10])[O:6][C@H:5]([C@H:7]([OH:9])[CH3:8])[CH2:4][O:3]1.[Cl:11][C:12]1[CH:17]=[C:16](Cl)[N:15]=[C:14]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])[N:13]=1.FC1C(F)=CC=CC=1CSC1N=C(NS(N2CCC2)(=O)=O)C=C(OC(CO)CO)N=1>C1COCC1.[H-].[Na+]>[Cl:11][C:12]1[CH:17]=[C:16]([O:9][C@@H:7]([C@@H:5]2[CH2:4][O:3][C:2]([CH3:10])([CH3:1])[O:6]2)[CH3:8])[N:15]=[C:14]([S:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=2[F:28])[N:13]=1

Participants

6

Reactant 3

HCID 11698344N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[2-hydroxy-1-(hydroxymethyl)ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamideHCID 53628362(R)-1-((S)-2,2-Dimethyl-1,3-dioxolan-4-yl)ethanolHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

Product 1

HCID 86619881HCID 86619881, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24758Sodium hydrideSolvent

Procedure

The subtitle compound was prepared according to the procedure outlined in example 1 step (iii) using (1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (prepared according to Liebigs, Ann. Chem. 1987, 7-14) (0.25 g) and 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step (0.53 g) in THF (20 mL) and 60% sodium hydride (80 mg). Crude material was purified by column chromatography on silica gel using EtOAc/isohexane (1:3) as eluent to give the subtitle compound as a clear, colourless oil. Yield: 0.37 g.

Workup

  1. customThe subtitle compound was prepared
  2. customCrude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8029fddd1f9a4860bc314dfbb6f0f9a8
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

Loading…