methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate → 3-[4-(Azetidin-1-ylcarbonyl)-2-chlorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methylpyrazin-2-yl)benzamide

HRID 20525Notes

Reaction equation

HRID 20525 reaction equation
OC1C=C(C=C(O[C@@H](C)CO)C=1)C(OC)=O.[N:17]1([C:21]([C:23]2[CH:57]=[CH:56][C:26]([O:27][C:28]3[CH:29]=[C:30]([CH:41]=[C:42]([O:44][C@@H:45]([CH3:55])[CH2:46][O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[CH:43]=3)[C:31]([NH:33][C:34]3[CH:39]=[N:38][C:37]([CH3:40])=[CH:36][N:35]=3)=[O:32])=[C:25](F)[CH:24]=2)=[O:22])[CH2:20][CH2:19][CH2:18]1.[Cl:59]C1C=C(C=CC=1F)C(N1CCC1)=O>>[N:17]1([C:21]([C:23]2[CH:57]=[CH:56][C:26]([O:27][C:28]3[CH:29]=[C:30]([CH:41]=[C:42]([O:44][C@@H:45]([CH3:55])[CH2:46][O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[CH:43]=3)[C:31]([NH:33][C:34]3[CH:39]=[N:38][C:37]([CH3:40])=[CH:36][N:35]=3)=[O:32])=[C:25]([Cl:59])[CH:24]=2)=[O:22])[CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 59127187methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoateHCID 593468603-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methylpyrazin-2-yl)benzamideHCID 59346868(Azetidin-1-yl)(3-chloro-4-fluorophenyl)methanone

Product 1

HCID 579047233-[4-(Azetidin-1-ylcarbonyl)-2-chlorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methylpyrazin-2-yl)benzamide

Procedure

3-[4-(Azetidin-1-ylcarbonyl)-2-chlorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methylpyrazin-2-yl)benzamide was prepared from methyl 3-hydroxy-5-[(1S)-2-hydroxy-1-methylethoxy]benzoate in an analogous fashion to 3-[4-(azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-(5-methylpyrazin-2-yl)benzamide but replacing 1-(3,4-difluorobenzoyl)azetidine with 1-(3-chloro-4-fluorobenzoyl)azetidine.

Sources & evidence

ORD record
ord-694c29f832194ee3a8c08d86f4310491
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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