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 2388754Notes

Reaction equation

HRID 2388754 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-1841913560374f468710e2cb6d0feede
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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