1-(1-Methyl-4-piperidinyl)piperazine → 4-chloro-N-(1-(2-(4-(1-methylpiperidin-4-yl)piperazin-1-yl)-2-oxoethyl)-1H-1,2,4-triazol-3-yl)cyclopenta-1,3-dienecarboxamide

HRID 2237570Notes

Reaction equation

HRID 2237570 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[N:14]=[CH:13][N:12]([CH2:15][C:16]([OH:18])=O)[N:11]=2)=[O:8])=[CH:4][CH:3]=1.[CH3:19][N:20]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH2:22][CH2:21]1>C1COCC1>[CH3:19][N:20]1[CH2:21][CH2:22][CH:23]([N:26]2[CH2:31][CH2:30][N:29]([C:16](=[O:18])[CH2:15][N:12]3[CH:13]=[N:14][C:10]([NH:9][C:7]([C:5]4[S:6][C:2]([Cl:1])=[CH:3][CH:4]=4)=[O:8])=[N:11]3)[CH2:28][CH2:27]2)[CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 59698827{3-[(5-Chloro-thiophene-2-carbonyl)-amino]-[1,2,4]triazol-1-yl}-acetic acid

Product 1

HCID 426431754-chloro-N-(1-(2-(4-(1-methylpiperidin-4-yl)piperazin-1-yl)-2-oxoethyl)-1H-1,2,4-triazol-3-yl)cyclopenta-1,3-dienecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using general method A, using THF instead of DMF as solvent, {3-[(5-chloro-thiophene-2-carbonyl)-amino]-[1,2,4]triazol-1-yl}-acetic acid (example 61.3) was reacted with 1-(N-methyl-4-piperidyl)-piperazine to give 5-chloro-thiophene-2-carboxylic acid (1-{2-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-1H-[1,2,4]triazol-3-yl)-amide. Off-white solid. MS 452.3 ([M+H]+)

Sources & evidence

ORD record
ord-ea10086bc7334762a55398fe34aa6978
Source dataset
uspto-grants-2010_05
Patent number
US07718659B2

Reaction notes

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