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

HRID 2035654Notes

Reaction equation

HRID 2035654 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.O[C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:39]=1[N:38]=[C:37]([C:40]1[N:44]3[CH:45]=[C:46]([C:49]#[N:50])[CH:47]=[CH:48][C:43]3=[N:42][N:41]=1)[CH:36]=[CH:35]2>>[C:49]([C:46]1[CH:47]=[CH:48][C:43]2[N:44]([C:40]([C:37]3[CH:36]=[CH:35][C:34]4[C:39](=[C:30]([O:9][C@H:8]5[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]5)[CH:31]=[CH:32][CH:33]=4)[N:38]=3)=[N:41][N:42]=2)[CH:45]=1)#[N:50]

Participants

3

Reactant 2

HCID 131731015cis-Tert-butyl 4-fluoro-5-(4-nitrophenylsulfonyloxy)azepane-1-carboxylateHCID 1364007703-(8-Hydroxyquinolin-2-yl)[1,2,4]triazolo[4,3-a]pyridine-6-carbonitrile

Product 1

HCID 131731024(trans)-Tert-butyl 4-(2-(6-cyano-[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 3-(8-hydroxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine-6-carbonitrile 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-0e24dbb3444940119800dc64594bcce4
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

Loading…