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

HRID 876458Notes

Reaction equation

HRID 876458 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 131731013trans-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 131731014(cis)-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

trans-tert-Butyl 4-fluoro-5-(4-nitrophenylsulfonyloxy)azepane-1-carboxylate (0.526 g, 1.26 mmol) and 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-6-fluoroquinolin-8-ol (0.320 g, 1.14 mmol) were slurried in CH3CN (5.5 mL). To this mixture was added 2-tert-butyl-1,1,3,3-tetramethylguanidine (0.276 mL, 1.37 mmol) dropwise. The mixture 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, and the solid was washed with water and hexanes and dried. This provided 0.460 g of the title compound (81%) as an off-white solid (>95% pure by HPLC). 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

Sources & evidence

ORD record
ord-2ee62493a4b74af8b390aad818083254
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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