3-((Tert-butyldiphenylsilyl)oxy)azetidine → 3-(tert-Butyl-diphenyl-silanyloxy)-azetidine-1-carboxylic acid [5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazole-2-yl]amide

HRID 2247377Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([N:13]=[C:14]=[O:15])=[N:10][C:9]=2[CH3:16])=[CH:4][C:3]=1[S:17]([CH3:20])(=[O:19])=[O:18].ClC1C=CC(C2SC(N)=NC=2C)=CC=1S(C)(=O)=O.[C:39]([Si:43]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[O:44][CH:45]1[CH2:48][NH:47][CH2:46]1)([CH3:42])([CH3:41])[CH3:40]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH:13][C:14]([N:47]3[CH2:46][CH:45]([O:44][Si:43]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=4)[C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[CH2:48]3)=[O:15])=[N:10][C:9]=2[CH3:16])=[CH:4][C:3]=1[S:17]([CH3:20])(=[O:18])=[O:19]

Participants

Conditions

Temperature: 120 °C

Procedure

A stirred solution of 5-(4-chloro-3-methanesulfonyl-phenyl)-2-isocyanato-4-methyl-thiazole [prepared by the same procedure as example 88a replacing 5-(3-fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (Example 72) in this example with 5-(4-chloro-3-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine (Example 83)] (0.2 g, 0.61 mmol) in DMF is treated with 3-(tert-butyl-diphenyl-silanyloxy)-azetidine (162b) (0.25 g, 0.8 mmol) and the reaction mixture is heated to 120° C. After 30 minutes, the reaction is complete. The product is purified by chromatography on silica eluting with ethyl acetate-hexane (1:2) to give the titled compound.

Workup

customThe product is purified by chromatography on silica eluting with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record: ord-39b4dda0712843b0bebdc85e339d366d
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687637B2

Reaction notes

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