4-Methylmorpholine → 5-(5-chloro-1-(3-fluoro-4-(trifluoromethoxy)phenyl)pentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15]([S-])=[NH:16])[CH:5]=[CH:6][C:7]=1[N:8]1[C:12]([CH3:13])=[N:11][CH:10]=[N:9]1.I.[Cl:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[C:30]([F:39])[CH:29]=1)[C:25](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:56][NH2:57]>>[Cl:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]([C:25]1[NH:57][N:56]=[C:15]([NH:14][C:4]2[CH:5]=[CH:6][C:7]([N:8]3[C:12]([CH3:13])=[N:11][CH:10]=[N:9]3)=[C:2]([F:1])[CH:3]=2)[N:16]=1)[C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:36])([F:37])[F:38])=[C:30]([F:39])[CH:29]=1Participants
7
Reactant 6
Product 1
Procedure
3-Fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.330 g, 0.839 mmol, from preparation C) and 6-chloro-2-(3-fluoro-4-(trifluoromethoxy)phenyl)hexanoic acid (0.345 g, 1.05 mmol, from preparation AY) were coupled [N-methylmorpholine (0.461 mL, 4.20 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.132 mL, 4.20 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, the crude product, 5-(5-chloro-1-(3-fluoro-4-(trifluoromethoxy)phenyl)pentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine was obtained as a brown solid. LC-MS (M+H)+ 542.1. The crude product was used in the next step without purification.
Sources & evidence
- ORD record
- ord-0d2e69adf61b4a1eb4d069f9ba2cf31b
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08349880B2
Reaction notes
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