4-Methylmorpholine → 5-(5-chloro-1-(4-(2,2-difluoroethoxy)phenyl)pentyl)-N-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-fluorophenyl)-1H-1,2,4-triazol-3-amine

HRID 1803288Notes

Reaction equation

HRID 1803288 reaction equation
I.[CH3:2][C:3]1[N:7]=[C:6]([CH3:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](SC)=[NH:17])=[CH:11][C:10]=2[F:20])[N:4]=1.[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH:38]([F:40])[F:39])=[CH:32][CH:31]=1)[C:27](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:57][NH2:58]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:27]1[NH:58][N:57]=[C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([N:5]3[C:6]([CH3:8])=[N:7][C:3]([CH3:2])=[N:4]3)=[C:10]([F:20])[CH:11]=2)[N:17]=1)[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH:38]([F:40])[F:39])=[CH:32][CH:31]=1

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 581101806-Chloro-2-(4-(2,2-difluoroethoxy)phenyl)hexanoic acidHCID 178504010HCID 178504010, compound

Product 1

HCID 866499325-(5-chloro-1-(4-(2,2-difluoroethoxy)phenyl)pentyl)-N-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-fluorophenyl)-1H-1,2,4-triazol-3-amine

Procedure

Methyl 4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-fluorophenylcarbamimidothioate, hydroiodide (600 mg, 1.47 mmol, from preparation T) and 6-chloro-2-(4-(2,2-difluoroethoxy)phenyl)hexanoic acid (475 mg, 1.55 mmol, from preparation AX) were coupled [N-methylmorpholine (0.810 mL, 7.37 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.231 mL, 7.37 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, crude 5-(5-chloro-1-(4-(2,2-difluoroethoxy)phenyl)pentyl)-N-(4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-3-fluorophenyl)-1H-1,2,4-triazol-3-amine was obtained as a brown gummy oil. LC-MS (M+H)+ 534.4.

Sources & evidence

ORD record
ord-ad0bbbb607f2414ca3a1de8ad83db760
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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