1-Azetidinesulfonamide → N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[(2-phenyl-1,3-dioxan-5-yl)thio]pyrimidin-4-yl]azetidine-1-sulfonamide

HRID 1024867Notes

Reaction equation

HRID 1024867 reaction equation
[N:1]1([S:5]([NH2:8])(=[O:7])=[O:6])[CH2:4][CH2:3][CH2:2]1.Cl[C:10]1[CH:15]=[C:14]([S:16][CH:17]2[CH2:22][O:21][CH:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:19][CH2:18]2)[N:13]=[C:12]([S:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:32]=2[F:38])[N:11]=1>>[F:38][C:32]1[C:33]([F:37])=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][S:29][C:12]1[N:11]=[C:10]([NH:8][S:5]([N:1]2[CH2:4][CH2:3][CH2:2]2)(=[O:7])=[O:6])[CH:15]=[C:14]([S:16][CH:17]2[CH2:18][O:19][CH:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:21][CH2:22]2)[N:13]=1

Participants

3

Reactant 2

HCID 450805661-AzetidinesulfonamideHCID 536283504-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2-phenyl-1,3-dioxan-5-yl)thio]pyrimidine2×

Product 1

HCID 53628349N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[(2-phenyl-1,3-dioxan-5-yl)thio]pyrimidin-4-yl]azetidine-1-sulfonamide

Procedure

The subtitle compound was prepared from azetidine-1-sulfonamide (prepared according to patent WO 2004/011443, 0.11 g) and 4-Chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-[(2-phenyl-1,3-dioxan-5-yl)thio]pyrimidine (the product of step i) (0.17 g) according to the procedure outlined in Example 1, step iv). The residue was purified by flash chromatography on silica gel, eluting with EtOAc/iso-hexane (2:8) to give the subtitle compound as a colourless oil. Yield: 0.11 g

Workup

  1. customThe residue was purified by flash chromatography on silica gel
  2. washeluting with EtOAc/iso-hexane (2:8)

Sources & evidence

ORD record
ord-fa4e51cca71d47de86b46959cc657cb3
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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