Pyridine → HCID 46861610, compound

HRID 1192824Notes

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][CH2:38][CH2:39][C:40]#[CH:41])[CH:32]=[CH:31][CH:30]=1)/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=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:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:34]=1)[CH2:39][C:40]#[CH:41]

Participants

Conditions

Temperature: 50 °C

Procedure

With ice cooling, 85 μl of trifluoromethanesulphonic anhydride were added to a solution of 100 mg (0.25 mmol) of but-3-yn-1-yl(Z)-{6-[({[2-(methylamino)-2-oxo-1-phenylethylidene]amino}oxy)methyl]pyridin-2-yl}carbamate (only Z diastereoisomer) and pyridine (81 μl, 4 eq.) in acetonitrile (2 ml). The mixture was heated at 50° C. for 2 h and then cooled to room temperature. Then, 49 mg of sodium azide were added and the mixture was stirred again at 50° C. for 2 h. The homogeneous orange solution was then cooled to room temperature and filtered over silica gel, and the silica gel filter layer was washed with 50 ml of EtOAc. The combined organic phases were concentrated by evaporation in vacuo, giving 87 mg (84% purity) of (Z)-but-3-yn-1-yl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate.

Workup

temperaturecooled to room temperature
temperatureThe homogeneous orange solution was then cooled to room temperature
filtrationfiltered over silica gel
filtrationthe silica gel filter layer
washwas washed with 50 ml of EtOAc
concentrationThe combined organic phases were concentrated by evaporation in vacuo

Sources & evidence

ORD record: ord-ffc05327e6704b97a5bd35c84c3a8547
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680283B2

Reaction notes

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