2-tert-Butyl-1,1,3,3-tetramethylguanidine → trans-Tert-butyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-yloxy)-5-fluoroazepane-1-carboxylate

HRID 2035626Notes

Reaction equation

HRID 2035626 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.[N:29]1[N:30]=[C:31]([C:38]2[CH:47]=[CH:46][C:45]3[C:40](=[C:41](O)[CH:42]=[C:43]([F:48])[CH:44]=3)[N:39]=2)[N:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=12.C(N=C(N(C)C)N(C)C)(C)(C)C>CC#N.O>[N:29]1[N:30]=[C:31]([C:38]2[CH:47]=[CH:46][C:45]3[C:40](=[C:41]([O:9][C@H:8]4[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]4)[CH:42]=[C:43]([F:48])[CH:44]=3)[N:39]=2)[N:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=12

Participants

6

Reactant 3

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 131731015cis-Tert-butyl 4-fluoro-5-(4-nitrophenylsulfonyloxy)azepane-1-carboxylateHCID 1363378052-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol

Product 1

HCID 131731016trans-Tert-butyl 4-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-yloxy)-5-fluoroazepane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

cis-tert-butyl 4-fluoro-5-(4-nitrophenylsulfonyloxy)azepane-1-carboxylate (0.484 g, 1.16 mmol) and 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol (0.300 g, 1.07 mmol) were slurried in CH3CN (5.0 mL). To this mixture was added 2-tert-butyl-1,1,3,3-tetramethylguanidine (0.259 mL, 1.28 mmol) dropwise. The dark solution was warmed to 40° C. and stirred overnight. The mixture was cooled to ambient temperature and diluted with water (10 mL) and stirred for 15 minutes, then filtered. The solid was washed with water and hexanes and dried in vacuo. The product was purified via column chromatography (10 to 50% Acetone/CH2Cl2) to provide the product as off-white solid. MS ESI (+) m/z 496.0 (M+1) detected.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. stirringstirred for 15 minutes
  3. filtrationfiltered
  4. washThe solid was washed with water and hexanes
  5. customdried in vacuo
  6. customThe product was purified via column chromatography (10 to 50% Acetone/CH2Cl2)

Sources & evidence

ORD record
ord-af6043936060475db69782a5ee6a6fc4
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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