4-Methylmorpholine → 4-(5-chloro-1-(3-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-1H-1,2,4-triazol-5-yl)pentyl)benzonitrile

HRID 1803257Notes

Reaction equation

HRID 1803257 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]([C:36]#[N:37])=[CH:32][CH:31]=1)[C:27](O)=O.CN1CCOCC1.C(N(CC)C(C)C)(C)C.[NH2:54][NH2:55]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=1)[C:27]1[NH:55][N:54]=[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

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 581101896-Chloro-2-(4-cyanophenyl)hexanoic acidHCID 178493236methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide

Product 1

HCID 668606784-(5-chloro-1-(3-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-1H-1,2,4-triazol-5-yl)pentyl)benzonitrile

Procedure

Methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide (1.0 g, 2.36 mmol, from preparation A) and 6-chloro-2-(4-cyanophenyl)hexanoic acid (0.741 g, 2.94 mmol, from preparation AU) were coupled [N-methylmorpholine (1.29 mL, 11.8 mmol) was substituted for N,N-diisopropylethylamine] and then reacted with hydrazine (0.370 mL, 11.8 mmol) using a procedure analogous to Step A of Example 13. After aqueous workup, 4-(5-chloro-1-(3-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylamino)-1H-1,2,4-triazol-5-yl)pentyl)benzonitrile was obtained. The crude product was used in the subsequent step without purification. LC-MS (M+H)+ 496.2.

Sources & evidence

ORD record
ord-0a9585cb97ee40978511f47fe8bc8f74
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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