4-Methylmorpholine → 5-(5-chloro-1-(4-(2,2,2-trifluoroethoxy)phenyl)pentyl)-N-(5-fluoro-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:15][C:16](SC)=[NH:17])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[N:12][C:11]([CH3:14])=[N:10]1.[Cl:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[CH:31][CH:30]=1)[C:26](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:57][NH2:58]>>[Cl:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:26]1[NH:58][N:57]=[C:16]([NH:15][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)=[CH:7][CH:6]=2)[N:17]=1)[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]([F:38])([F:39])[F:40])=[CH:31][CH:30]=1Participants
6
Reactant 5
Product 1
Procedure
Methyl 3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.750 g, 1.91 mmol, from preparation Q) and 6-chloro-2-(4-(2,2,2-trifluoroethoxy)phenyl)hexanoic acid (0.650 g, 2.00 mmol, from preparation AW) were coupled [N-methylmorpholine (1.05 mL, 9.54 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.300 mL, 9.54 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, 5-(5-chloro-1-(4-(2,2,2-trifluoroethoxy)phenyl)pentyl)-N-(5-fluoro-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)+ 538.5.
Sources & evidence
- ORD record
- ord-26dcedff61c14cd69ae2b1f53b0585f6
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349880B2
Reaction notes
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