4-Methylmorpholine → HCID 86672060, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([OH:22])=[O:21])[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl[C:24]([O:26][CH2:27][CH:28]([CH3:30])C)=O.C[N:32]1[CH2:37][CH2:36]OC[CH2:33]1.[CH3:38][OH:39].ClCCl>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([O:22][C:38](=[O:39])/[CH:36]=[CH:37]\[N:32]3[CH:33]=[N:17][C:13]([C:5]4[CH:6]=[C:30]([C:9]([F:12])([F:11])[F:10])[CH:28]=[C:27]([O:26][CH3:24])[CH:4]=4)=[N:14]3)=[O:21])[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 500 mL, 3N round-bottomed flask equipped with nitrogen inlet, and a rubber septum, (Z)-3-(3-(3-methoxy-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylic acid (25 g, 1.0 eq.) was dissolved in THF (200 mL). The reaction mixture was cooled to 0° C. To this reaction mixture was added Isobutyl chloroformate (24.9 mL, 2.4 eq.) and 4-methylmorpholine (18.5 mL, 2.1 eq.). The reaction mixture was maintained at 0° C. for 1 h. The progress of the reaction was followed by TLC analysis on silica gel with 10% MeOH-dichloromethane as mobile phase. SM Rf=0.20 and Product Rf=0.6. Reaction mixture was filtered through celite bed. The filtrate was used for next step without any work up and purification.
Workup
- customIn a 500 mL, 3N round-bottomed flask equipped with nitrogen inlet
- temperatureThe reaction mixture was maintained at 0° C. for 1 h
- customReaction mixture
- filtrationwas filtered through celite bed
- custompurification
Sources & evidence
- ORD record
- ord-074b5eb25d6344dcaa1078227077bb80
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303000B2
Reaction notes
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