4-Methylmorpholine → 5-(5-chloro-1-(4-(trifluoromethoxy)phenyl)pentyl)-N-(3-fluoro-5-methoxy-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:17][C:18](SC)=[NH:19])[CH:6]=[C:7]([O:15][CH3:16])[C:8]=1[N:9]1[CH:13]=[N:12][C:11]([CH3:14])=[N:10]1.[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=1)[C:28](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:58][NH2:59]>>[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([C:28]1[NH:59][N:58]=[C:18]([NH:17][C:5]2[CH:6]=[C:7]([O:15][CH3:16])[C:8]([N:9]3[CH:13]=[N:12][C:11]([CH3:14])=[N:10]3)=[C:3]([F:2])[CH:4]=2)[N:19]=1)[C:31]1[CH:36]=[CH:35][C:34]([O:37][C:38]([F:39])([F:40])[F:41])=[CH:33][CH:32]=1Participants
6
Reactant 5
Product 1
Procedure
Methyl 3-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.575 g, 1.36 mmol, from preparation 5) and 6-chloro-2-(4-(trifluoromethoxy)phenyl)hexanoic acid (0.528 g, 1.70 mmol, from preparation AI) were coupled [N-methylmorpholine (0.747 mL, 6.79 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.213 mL, 6.80 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, 5-(5-chloro-1-(4-(trifluoromethoxy)phenyl)pentyl)-N-(3-fluoro-5-methoxy-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)+ 554.2.
Sources & evidence
- ORD record
- ord-89454c749aff4c978890f17a76d34985
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349880B2
Reaction notes
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