4-Methylmorpholine → HCID 66858579, compound

HRID 1803321Notes

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][CH:33]=[CH:32][CH:31]=1)[C:27](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:52][NH2:53]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:27]1[NH:53][N:52]=[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][CH:33]=[CH:32][CH:31]=1

Participants

Reactant 5

HCID 79724-Methylmorpholine

HCID 9321Hydrazine

HCID 81531Diisopropylethylamine

HCID 58110045HCID 58110045, compound

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

Product 1

HCID 66858579HCID 66858579, compound

Procedure

Methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide (0.500 g, 1.18 mmol), from preparation A) and 6-chloro-2-phenylhexanoic acid (0.294 g, 1.30 mmol, from preparation AAO) were coupled [N-methylmorpholine (0.647 mL, 5.89 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.148 mL, 4.71 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, 5-(5-chloro-1-phenylpentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-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)+ 471.3.

Sources & evidence

ORD record: ord-cb05ade040144098bbf8a45875cecc60
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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