((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonate → N-((2S)-1-((2-(5-(((1R)-2,2-difluorocyclopropyl)methoxy)pyridin-2-yl)-7-fluoro[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

HRID 2277317Notes

Reaction equation

HRID 2277317 reaction equation
C(O[C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]3[C:22]([F:23])=[C:21]([O:24][CH2:25][C@@H:26]([NH:28][C:29](=[O:31])[CH3:30])[CH3:27])[N:20]=[CH:19][C:18]=3[N:32]=2)=[N:13][CH:14]=1)C1C=CC=CC=1.[N+](C1C=CC(S([O:45][CH2:46][C@H:47]2[CH2:49][C:48]2([F:51])[F:50])(=O)=O)=CC=1)([O-])=O>>[F:51][C:48]1([F:50])[CH2:49][C@@H:47]1[CH2:46][O:45][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]3[C:22]([F:23])=[C:21]([O:24][CH2:25][C@@H:26]([NH:28][C:29](=[O:31])[CH3:30])[CH3:27])[N:20]=[CH:19][C:18]=3[N:32]=2)=[N:13][CH:14]=1

Participants

3

Reactant 2

HCID 86731320((1R)-2,2-difluorocyclopropyl)methyl 4-nitrobenzenesulfonateHCID 86731403N-((2S)-1-((2-(5-(benzyloxy)pyridin-2-yl)-7-fluoro[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

Product 1

HCID 86731402N-((2S)-1-((2-(5-(((1R)-2,2-difluorocyclopropyl)methoxy)pyridin-2-yl)-7-fluoro[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

Procedure

Using N-((2S)-1-((2-(5-(benzyloxy)pyridin-2-yl)-7-fluoro[1,3]oxazolo[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 Step A of Example 4 and Example 5, the title compound was obtained.

Sources & evidence

ORD record
ord-9964664dcf674f6f89ca20cc5a5bc0b3
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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