4-Methylmorpholine → 5-(4-chloro-1-(4-(trifluoromethoxy)phenyl)butyl)-N-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

HRID 1803297Notes

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][CH:24]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=1)[C:25](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:55][NH2:56]>>[Cl:20][CH2:21][CH2:22][CH2:23][CH:24]([C:25]1[NH:56][N:55]=[C:16]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH:13]=[N:12][C:11]([CH3:14])=[N:10]3)=[C:3]([F:2])[CH:4]=2)[N:17]=1)[C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:36])([F:37])[F:38])=[CH:30][CH:29]=1

Participants

Reactant 5

HCID 79724-Methylmorpholine

HCID 9321Hydrazine

HCID 81531Diisopropylethylamine

HCID 581100785-Chloro-2-(4-(trifluoromethoxy)phenyl)pentanoic acid

HCID 178504008HCID 178504008, compound

Product 1

HCID 668603415-(4-chloro-1-(4-(trifluoromethoxy)phenyl)butyl)-N-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

Procedure

Methyl 3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.578 g, 1.471 mmol), from preparation Q) and 5-chloro-2-(4-(trifluoromethoxy)phenyl)pentanoic acid (0.480 g, 1.62 mmol, from preparation AAK) were coupled [N-methylmorpholine (0.81 mL, 7.36 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.185 mL, 5.88 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, 5-(4-chloro-1-(4-(trifluoromethoxy)phenyl)butyl)-N-(3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine was obtained as a brown residue. The crude product was used in the next step without purification. LC-MS (M+H)+ 510.1.

Sources & evidence

ORD record: ord-20b737ae484f498290c937b676f3138c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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