Methanesulfonic Acid → HCID 57524120, compound

HRID 623813Notes

Reaction equation

HRID 623813 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[CH:11][N:10](/[CH:13]=[CH:14]\[C:15]([NH:17][NH2:18])=[O:16])[N:9]=2)[CH:5]=[C:4]([O:19][CH3:20])[N:3]=1.[CH:21](OC)(OC)OC.CS(O)(=O)=O.CCOC(C)=O.CCCCCC>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[CH:11][N:10](/[CH:13]=[CH:14]\[C:15]3[O:16][CH:21]=[N:18][N:17]=3)[N:9]=2)[CH:5]=[C:4]([O:19][CH3:20])[N:3]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 9005Trimethyl orthoformateHCID 21226206Ethyl acetate hexaneHCID 86672062HCID 86672062, compound

Product 1

HCID 57524120HCID 57524120, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100-mL, 3N round-bottomed flask equipped with Thermometer pocket fitted with nitrogen inlet, condenser and a rubber septum, (Z)-3-(3-(2-chloro-6-methoxypyridin-4-yl)-1H-1,2,4-triazol-1-yl)acrylohydrazide (0.7 g, 1.0 eq.), trimethyl orthoformate (0.3 mL, 1.1 eq.) and methane sulfonic acid (0.07 mL, 0.5 eq) was dissolved in THF (70 mL) resulting reaction mixture was stir at reflux temperature. The progress of the reaction was followed by TLC analysis on silica gel with 80% EtOAc-hexane as mobile phase which shows that starting material was consumed after 3 h. Reaction was quenched by water, solid material was observed that was filter on Buchner funnel to give crude material (0.490 g). The crude material was subjected to combiflash purification using ethyl acetate:hexane as mobile phase; Yield: 0.03 g (4.14%); (Z)-2-(2-(3-(2-chloro-6-methoxypyridine-4-yl)-1H-1,2,4-triazol-1-yl)vinyl)-1,3,4-oxadiazole: 1H NMR: (400 MHz, DMSO) δ=9.45 (s, 1H), 9.36 (s, 1H), 7.737-7.762 (d, J=10 Hz, 1H), 7.48 (s, 1H), 7.24 (s, 1H), 6.719-6.745 (d, J=10.4 Hz, 1H), 3.92 (s, 3H). LC-MS: Calculated for C12H9ClN6O2 (M+H)+ 304.69 Found: 304.81 Retention time: 3.354 min (100%).

Workup

  1. customIn a 100-mL, 3N round-bottomed flask equipped with Thermometer pocket
  2. customfitted with nitrogen inlet, condenser
  3. customresulting
  4. customreaction mixture
  5. temperatureat reflux temperature
  6. customwas consumed after 3 h
  7. customReaction
  8. customwas quenched by water, solid material
  9. filtrationthat was filter on Buchner funnel

Sources & evidence

ORD record
ord-71d28e8a864646c8a268e9726ea6faf2
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

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