Methanol → 7-[5-(5-Chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-3-(2-thienyl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3]thiazine

HRID 2102308Notes

Reaction equation

HRID 2102308 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[C:12]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[N:11][N:10]=[C:9]1[S:18][CH2:19][C:20]1[N:24]=[C:23]([C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=2[F:32])[O:22][N:21]=1)(=O)=O.[H-].[Na+].CO>CN(C=O)C>[Cl:31][C:29]1[CH:28]=[CH:27][C:26]([F:32])=[C:25]([C:23]2[O:22][N:21]=[C:20]([CH:19]3[S:18][C:9]4=[N:10][N:11]=[C:12]([C:13]5[S:14][CH:15]=[CH:16][CH:17]=5)[N:8]4[CH2:7][CH2:6]3)[N:24]=2)[CH:30]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 866025852-[3-({[5-(5-Chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}thio)-5-(2-thienyl)-4H-1,2,4-triazol-4-yl]ethyl methanesulfonate

Product 1

HCID 113391437-[5-(5-Chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-3-(2-thienyl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3]thiazineYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[3-({[5-(5-chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}thio)-5-(2-thienyl)-4H-1,2,4-triazol-4-yl]ethyl methanesulfonate (43 mg) in DMF (2 ml) was added sodium hydride (10 mg) at −78° C. while stirring. The mixture was allowed to come to r.t. and stirred for another 3 h before addition of MeOH (1 ml) and concentration onto silica gel. Purification by chromatography on silica gel using DCM:EA:MeOH 70:30:2 as eluent provided 2.8 mg of the title compound. 1H NMR: 8.07 (dd, 1H), 7.56 (m, 1H), 7.51 (dd, 1H), 7.47 (dd, 1H), 7.17-7.23 (m, 2H), 4.86 (dd, 1H), 4.60 (m, 1H), 4.38 (m, 1H), 2.82 (m, 2H)

Workup

  1. customto come to r.t.
  2. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-1f72e21a05ad4dd3b14d1f864f1f52b9
Source dataset
uspto-grants-2009_08
Patent number
US07576077B2

Reaction notes

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