4-Methylmorpholine → 5-(5-chloro-1-(4-isopropoxyphenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine

HRID 1803283Notes

Reaction equation

HRID 1803283 reaction equation
I.[Cl:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](SC)=[NH:16])=[CH:10][C:9]=2[O:19][CH3:20])[CH:7]=1.[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([CH3:39])[CH3:38])=[CH:32][CH:31]=1)[C:27](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:56][NH2:57]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:27]1[NH:57][N:56]=[C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([N:6]3[CH:7]=[C:3]([Cl:2])[N:4]=[CH:5]3)=[C:9]([O:19][CH3:20])[CH:10]=2)[N:16]=1)[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([CH3:39])[CH3:38])=[CH:32][CH:31]=1

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 581100936-Chloro-2-(4-isopropoxyphenyl)hexanoic acidHCID 178493236methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide

Product 1

HCID 668587465-(5-chloro-1-(4-isopropoxyphenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amineYield 43%

Procedure

Methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide (1.50 g, 3.53 mmol, from preparation A) and 6-chloro-2-(4-isopropoxyphenyl)hexanoic acid (1.26 g, 4.42 mmol, from preparation AV) were coupled [N-methylmorpholine (2.00 mL, 17.7 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.556 mL, 17.7 mmol) using a procedure analogous to Step A of Example 13. The crude products were purified using silica gel chromatography (50% ethyl acetate/chloroform) to afford 5-(5-chloro-1-(4-isopropoxyphenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (805 mg, 1.52 mmol, 43% yield) as an off-white solid. LC-MS (M+H)+ 529.3.

Workup

  1. customThe crude products were purified

Sources & evidence

ORD record
ord-b02276e056e445d0b6ee3a4c7e5652d8
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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