Potassium Carbonate → Methyl 2-(((1-(5-amino-4H-1,2,4-triazol-3-yl)piperidin-4-yl)(4-chlorophenethyl)amino)-methyl)benzoate

HRID 59784Notes

Reaction equation

HRID 59784 reaction equation
Cl.[Cl:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][CH2:8][N:9]([CH2:16][C:17]2[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=2[C:19]([O:21][CH3:22])=[O:20])[CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[C:35]([N:37]=[C:38]([N:40]1CCNCC1)[S-])#[N:36].O.[NH2:47]N>>[NH2:47][C:38]1[NH:37][C:35]([N:13]2[CH2:14][CH2:15][CH:10]([N:9]([CH2:16][C:17]3[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=3[C:19]([O:21][CH3:22])=[O:20])[CH2:8][CH2:7][C:6]3[CH:27]=[CH:28][C:3]([Cl:2])=[CH:4][CH:5]=3)[CH2:11][CH2:12]2)=[N:36][N:40]=1

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 121410305HCID 121410305, compoundHCID 131737066N-cyanopiperazine-1-carbimidothioate

Product 1

HCID 178497630Methyl 2-(((1-(5-amino-4H-1,2,4-triazol-3-yl)piperidin-4-yl)(4-chlorophenethyl)amino)-methyl)benzoate

Procedure

Methyl 2-(((4-chlorophenethyl)(piperidin-4-yl)amino)methyl)benzoate hydrochloride obtained in Step 2 was reacted with K2CO3 and S,S′-dimethyl-N-cyano-dithioiminocarbonate, followed by the cyclization of the intermediate (N-cyanopiperazine-1-carbimidothioate) with hydrazine monohydrate in a manner described in Procedure 3. ESI MS for C24H29ClN6O2: calculated 468.99. found 469.4/471.4 (M+1), 467.3/469.3 (M−1).

Sources & evidence

ORD record
ord-ac3dfa39f10e4c508c4d38248688f596
Source dataset
uspto-grants-2016_09
Patent number
US09440953B2

Reaction notes

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