Pyridine → HCID 75235279, compound

HRID 1192822Notes

Reaction equation

HRID 1192822 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:16][NH:17][C:18](=O)[C:19](=[N:26][O:27][CH2:28][C:29]1[N:34]=[C:33]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])(C)C)[CH:32]=[CH:31][CH:30]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1[CH:49]=[CH:48]C=CC=1.[N-:50]=[N+:51]=[N-:52].[Na+]>C(#N)C>[CH2:38]([O:37][C:36](=[O:42])[NH:35][C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:28][O:27][N:26]=[C:19]([C:18]2[N:17]([CH3:16])[N:52]=[N:51][N:50]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:34]=1)[CH2:41][C:48]#[CH:49]

Participants

6

Reactant 4

HCID 1049PyridineHCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 86681505HCID 86681505, compound2×

Product 1

HCID 75235279HCID 75235279, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At −10° C., trifluoromethanesulphonic anhydride (42 μl, 1.5 eq.) was added to a solution of 63 mg (0.16 mmol) of tert-butyl{6-[({[2-(methylamino)-2-oxo-1-phenylethylidene]amino}oxy)methyl]pyridin-2-yl}carbamate (36:64 mixture of Z and E diastereoisomers) and pyridine (53 μl, 4 eq.) in acetonitrile (1.6 ml). After warming to room temperature, the mixture was stirred for a further 1 h at 50° C. and then cooled again to room temperature. Then, 32 mg of sodium azide were added and the mixture was stirred again at 50° C. for one hour. The mixture was cooled to room temperature and a sample was analyzed using LCMS. The sample comprises 87% of the expected tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (36:64 mixture of Z and E diastereoisomers).

Workup

  1. temperaturecooled again to room temperature
  2. stirringthe mixture was stirred again at 50° C. for one hour
  3. temperatureThe mixture was cooled to room temperature

Sources & evidence

ORD record
ord-ca7cf056197241dc99e20bcd0d90e66e
Source dataset
uspto-grants-2014_03
Patent number
US08680283B2

Reaction notes

Loading…