Acetic Acid → 4-(5-Oxo-3-pyrazin-2-yl-2,5-dihydro-pyrazol-1-yl)-N-(1,2,2,6,6-pentamethyl-piperidin-4-yl)-benzamide

HRID 1695961Notes

Reaction equation

HRID 1695961 reaction equation
O=[C:2]([C:9]1[CH:14]=[N:13][CH:12]=[CH:11][N:10]=1)[CH2:3][C:4]([O:6]CC)=O.[NH:15]([C:17]1[CH:36]=[CH:35][C:20]([C:21]([NH:23][CH:24]2[CH2:29][C:28]([CH3:31])([CH3:30])[N:27]([CH3:32])[C:26]([CH3:34])([CH3:33])[CH2:25]2)=[O:22])=[CH:19][CH:18]=1)[NH2:16].C(O)(=O)C>C(O)C>[O:6]=[C:4]1[N:15]([C:17]2[CH:36]=[CH:35][C:20]([C:21]([NH:23][CH:24]3[CH2:25][C:26]([CH3:33])([CH3:34])[N:27]([CH3:32])[C:28]([CH3:31])([CH3:30])[CH2:29]3)=[O:22])=[CH:19][CH:18]=2)[NH:16][C:2]([C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6454349Ethyl beta-oxopyrazinepropionateHCID 595155764-Hydrazino-N-(1,2,2,6,6-pentamethyl-piperidin-4-yl)-benzamide

Product 1

HCID 595155774-(5-Oxo-3-pyrazin-2-yl-2,5-dihydro-pyrazol-1-yl)-N-(1,2,2,6,6-pentamethyl-piperidin-4-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Oxo-3-pyrazin-2-yl-propionic acid, ethyl ester (78 mg) and 4-hydrazino-N-(1,2,2,6,6-pentamethyl-piperidin-4-yl)-benzamide (141 mg) were dissolved in ethanol (3.5 ml) and acetic acid (0.5 ml) and the solution stirred at 65° C. for 2 h. Concentration in vacuo and purification by HPLC gave the expected product. LC/MS: main peak is product (m/z: 434)

Workup

  1. concentrationConcentration
  2. customin vacuo and purification by HPLC

Sources & evidence

ORD record
ord-044c7100748846ffa47f7fb2af1c1361
Source dataset
uspto-grants-2012_04
Patent number
US08163757B2

Reaction notes

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