4-Methylmorpholine → 5-(5-chloro-1-(4-(trifluoromethylsulfonyl)phenyl)pentyl)-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

HRID 1803301Notes

Reaction equation

HRID 1803301 reaction equation
I.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:16][C:17](SC)=[NH:18])[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[N:13][C:12]([CH3:15])=[N:11]1.[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([C:39]([F:42])([F:41])[F:40])(=[O:38])=[O:37])=[CH:32][CH:31]=1)[C:27](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:59][NH2:60]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:27]1[NH:60][N:59]=[C:17]([NH:16][C:6]2[CH:7]=[CH:8][C:9]([N:10]3[CH:14]=[N:13][C:12]([CH3:15])=[N:11]3)=[C:4]([O:3][CH3:2])[CH:5]=2)[N:18]=1)[C:30]1[CH:31]=[CH:32][C:33]([S:36]([C:39]([F:42])([F:40])[F:41])(=[O:37])=[O:38])=[CH:34][CH:35]=1

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 581101486-Chloro-2-(4-(trifluoromethylsulfonyl)phenyl)hexanoic acidHCID 178493238HCID 178493238, compound

Product 1

HCID 668585645-(5-chloro-1-(4-(trifluoromethylsulfonyl)phenyl)pentyl)-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

Procedure

Methyl 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.250 g, 0.617 mmol), from preparation F) and 6-chloro-2-(4-(trifluoromethylsulfonyl)phenyl)hexanoic acid (0.221 g, 0.617 mmol, from preparation AAM) were coupled [N-methylmorpholine (0.339 mL, 3.08 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.069 mL, 2.21 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, 5-(5-chloro-1-(4-(trifluoromethylsulfonyl)phenyl)pentyl)-N-(3-methoxy-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)+ 584.0.

Sources & evidence

ORD record
ord-d4f31d9c2987465b8dcf3ba1358a4c8a
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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