4-Methylmorpholine → HCID 66858196, compound

HRID 1803328Notes

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.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH2:32][CH2:33][CH2:34][CH2:35][Cl:36])[C:29](O)=O)=[CH:24][CH:23]=1.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:53][NH2:54]>>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([C:29]2[NH:54][N:53]=[C:15]([NH:14][C:11]3[CH:12]=[CH:13][C:8]([N:6]4[CH:7]=[C:3]([Cl:2])[N:4]=[CH:5]4)=[C:9]([O:19][CH3:20])[CH:10]=3)[N:16]=2)[CH2:32][CH2:33][CH2:34][CH2:35][Cl:36])=[CH:24][CH:23]=1

Participants

Reactant 5

HCID 79724-Methylmorpholine

HCID 9321Hydrazine

HCID 81531Diisopropylethylamine

HCID 58109999HCID 58109999, compound

HCID 178493236methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide

Product 1

HCID 66858196HCID 66858196, compoundYield 46.9%

Procedure

Methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide (4.0 g, 9.42 mmol, from preparation A) and 2-(4-bromophenyl)-6-chlorohexanoic acid (3.60 g, 11.77 mmol, from preparation AT) were coupled [N-methylmorpholine (5.18 mL, 47.1 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (1.48 mL, 47.1 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, crude 5-(1-(4-bromophenyl)-5-chloropentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (2.43 g, 4.42 mmol, 46.9% yield) was obtained as a brown foamy solid The crude product was used in next step without purification. LC-MS (M+H)+ 551.2.

Sources & evidence

ORD record: ord-d13a53cc873e41a7ad9f423ac1a6a5b2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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