Cyclohexaneacetic acid → 2-cyclohexyl-N-[1-(3-{[4-(methyloxy)phenyl]amino)-1,2,4-triazin-6-yl)ethyl]acetamide
Reaction equation
Br[C:2]1S[C:5]([C:7]([NH:9][CH:10]([C:12]2[N:17]=[N:16][C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:14][CH:13]=2)[CH3:11])=[O:8])=[CH:4][CH:3]=1.N[CH:28]([C:30]1N=NC(NC2C=CC(OC)=CC=2)=NC=1)[CH3:29].C1(CC(O)=O)CCCCC1>>[CH:4]1([CH2:5][C:7]([NH:9][CH:10]([C:12]2[N:17]=[N:16][C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:14][CH:13]=2)[CH3:11])=[O:8])[CH2:30][CH2:28][CH2:29][CH2:2][CH2:3]1Participants
4
Reactant 3
Product 1
Procedure
In a similar manner as described for Intermediate 48, using 6-(1-aminoethyl)-N-[4-(methyloxy)phenyl]-1,2,4-triazin-3-amine (Intermediate 47) (100 mg, 0.41 mmol), and cyclohexylacetic acid (64 mg, 0.45 mmol), except that the reaction was stirred for 4 h and the crude reaction mixture reduced under vacuum, partitioned between dichloromethane and saturated sodium bicarbonate solution and the layers separated. The aqueous was re-extracted with dichloromethane and the combined organic layers washed with brine, dried with magnesium sulfate, filtered and reduced to give 2-cyclohexyl-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]acetamide (100 mg) as a yellow solid. MS m/z 370 (M+1).
Workup
- customthe crude reaction mixture
- custompartitioned between dichloromethane and saturated sodium bicarbonate solution
- customthe layers separated
- extractionThe aqueous was re-extracted with dichloromethane
- washthe combined organic layers washed with brine
- dry with materialdried with magnesium sulfate
- filtrationfiltered
Sources & evidence
- ORD record
- ord-7962f0205e674bdca6e94f234e448667
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07462614B2
Reaction notes
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