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 1958920Notes

Reaction equation

HRID 1958920 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-1db891078c5c475185670743dbf1eed9
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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