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

HRID 1803303Notes

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]([O:36][CH2:37][CH3:38])=[CH:32][CH:31]=1)[C:27](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:55][NH2:56]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:27]1[NH:56][N:55]=[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]([O:36][CH2:37][CH3:38])=[CH:34][CH:35]=1

Participants

Reactant 5

HCID 79724-Methylmorpholine

HCID 9321Hydrazine

HCID 81531Diisopropylethylamine

HCID 581101156-Chloro-2-(4-ethoxyphenyl)hexanoic acid

HCID 178493238HCID 178493238, compound

Product 1

HCID 668597835-(5-chloro-1-(4-ethoxyphenyl)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 (0.500 g, 1.23 mmol), from preparation F) and 6-chloro-2-(4-ethoxyphenyl)hexanoic acid (0.367 g, 1.36 mmol, from preparation AAN) were coupled [N-methylmorpholine (0.678 mL, 6.17 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.155 mL, 4.94 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, 5-(5-chloro-1-(4-ethoxyphenyl)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)+ 496.2.

Sources & evidence

ORD record: ord-6f99368a734d487794c3ba5b9d3abf30
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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