((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonate → N-((2S)-1-((2-(4-(((1R)-2,2-difluorocyclopropyl)methoxy)phenyl)[1,3]thiazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

HRID 2277313Notes

Reaction equation

HRID 2277313 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:15]=[C:14]([O:16][CH2:17][C@@H:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])[N:13]=[CH:12][C:11]=3[N:24]=2)=[CH:4][CH:3]=1.[N+](C1C=CC(S(O[CH2:38][C@H:39]2[CH2:41][C:40]2([F:43])[F:42])(=O)=O)=CC=1)([O-])=O>>[F:42][C:40]1([F:43])[CH2:41][C@@H:39]1[CH2:38][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:15]=[C:14]([O:16][CH2:17][C@@H:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])[N:13]=[CH:12][C:11]=3[N:24]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 86731320((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonateHCID 136341406N-((2S)-1-((2-(4-hydroxyphenyl)[1,3]thiazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

Product 1

HCID 86731398N-((2S)-1-((2-(4-(((1R)-2,2-difluorocyclopropyl)methoxy)phenyl)[1,3]thiazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

Procedure

Using N-((2S)-1-((2-(4-hydroxyphenyl)[1,3]thiazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide and ((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonate, and in the same manner as in Example 5, the title compound was obtained.

Sources & evidence

ORD record
ord-61215e322f6b4f5186ca0a3b3b8ebe45
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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