cis-Tert-butyl 4-fluoro-5-(4-nitrophenylsulfonyloxy)azepane-1-carboxylate → trans-Tert-butyl 4-(2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-5-fluoroazepane-1-carboxylate

HRID 876489Notes

Reaction equation

HRID 876489 reaction equation
[F:1][C@H:2]1[C@@H:8]([O:9]S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)[CH2:7][CH2:6][N:5]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:4][CH2:3]1.[CH:29]1([C:32]2[CH:33]=[CH:34][C:35]3[N:36]([C:38]([C:41]4[CH:50]=[CH:49][C:48]5[C:43](=[C:44](O)[CH:45]=[CH:46][CH:47]=5)[N:42]=4)=[N:39][N:40]=3)[CH:37]=2)[CH2:31][CH2:30]1>>[CH:29]1([C:32]2[CH:33]=[CH:34][C:35]3[N:36]([C:38]([C:41]4[CH:50]=[CH:49][C:48]5[C:43](=[C:44]([O:9][C@H:8]6[C@H:2]([F:1])[CH2:3][CH2:4][N:5]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:6][CH2:7]6)[CH:45]=[CH:46][CH:47]=5)[N:42]=4)=[N:39][N:40]=3)[CH:37]=2)[CH2:31][CH2:30]1

Participants

3

Reactant 2

HCID 131731015cis-Tert-butyl 4-fluoro-5-(4-nitrophenylsulfonyloxy)azepane-1-carboxylateHCID 1363378082-(6-Cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol

Product 1

HCID 131731021trans-Tert-butyl 4-(2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-5-fluoroazepane-1-carboxylate

Procedure

Prepared according to the method of Example 90 using cis-tert-butyl 4-fluoro-5-(4-nitrophenylsulfonyloxy)azepane-1-carboxylate in place of trans-tert-butyl 4-fluoro-5-(4-nitrophenylsulfonyloxy)azepane-1-carboxylate and 2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol in place of 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol in Step C and running the reaction at 50° C.

Workup

  1. customPrepared
  2. customthe reaction at 50° C.

Sources & evidence

ORD record
ord-c9f4c85bba034f0d90a1b56da4a96a41
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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