4-Methylmorpholine → 5-(5-chloro-1-(4-(trifluoromethoxy)phenyl)pentyl)-N-(3,5-difluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine
Reaction equation
I.[F:2][C:3]1[CH:4]=[C:5]([NH:16][C:17](SC)=[NH:18])[CH:6]=[C:7]([F:15])[C:8]=1[N:9]1[CH:13]=[N:12][C:11]([CH3:14])=[N:10]1.[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=1)[C:27](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:57][NH2:58]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:27]1[NH:58][N:57]=[C:17]([NH:16][C:5]2[CH:4]=[C:3]([F:2])[C:8]([N:9]3[CH:13]=[N:12][C:11]([CH3:14])=[N:10]3)=[C:7]([F:15])[CH:6]=2)[N:18]=1)[C:30]1[CH:35]=[CH:34][C:33]([O:36][C:37]([F:38])([F:39])[F:40])=[CH:32][CH:31]=1Participants
6
Reactant 5
Product 1
Procedure
Methyl 3,5-difluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.942 g, 2.92 mmol, from preparation R) and 6-chloro-2-(4-(trifluoromethoxy)phenyl)hexanoic acid (0.890 g, 2.86 mmol, from preparation AI) were coupled [N-methylmorpholine (0.1.26 mL, 11.0 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.360 mL, 11.5 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, crude 5-(5-chloro-1-(4-(trifluoromethoxy)phenyl)pentyl)-N-(3,5-difluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine was obtained as a brown solid. The crude product was used in the next step without purification. LC-MS (M+H)+ 542.1.
Sources & evidence
- ORD record
- ord-5628737b83de44fc9a126c24f208ef15
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349880B2
Reaction notes
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