Pyrazole → HCID 69999767, compound

HRID 1634824Notes

Reaction equation

CCCCCC.[H-].[K+].[NH:9]1[CH:13]=[CH:12][CH:11]=[N:10]1.[C:14]([O:18][C:19](=[O:38])[NH:20][CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([S:28]([C:31]2[CH:36]=[CH:35][C:34](N)=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH2:24][CH2:23]1)([CH3:17])([CH3:16])[CH3:15]>CN(C=O)C.O>[C:14]([O:18][C:19](=[O:38])[NH:20][CH2:21][CH:22]1[CH2:23][CH2:24][N:25]([S:28]([C:31]2[CH:36]=[CH:35][C:34]([N:9]3[CH:13]=[CH:12][CH:11]=[N:10]3)=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH2:26][CH2:27]1)([CH3:17])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred mixture of hexane washed potassium hydride (0.08 g, 2 mmol) in 5 mL of DMF was added pyrazole (0.136 g, 2 mmol) in one portion. Stirring was continued until gas evolution ceased. A solution of [1-(4-aminobenzenesulfonyl)-piperidin-4-ylmethyl]-carbamic acid t-butyl ester (0.745 g, 2 mmol) in 5 mL DMF was added and the solution was heated at 70° C. overnight. The reaction mixture was poured into water and the solids formed collected and dried (high vac). The crude product was purified by flash chromatography (silica Merck 60, CH2Cl2—CH3OH, 19:1) to give 0.258 g of the product as a white solid.

Workup

customthe solids formed
customcollected
customdried (high vac)
customThe crude product was purified by flash chromatography (silica Merck 60, CH2Cl2—CH3OH, 19:1)

Sources & evidence

ORD record: ord-7f916db2654546c5be3e70a24cecb914
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506901B2

Reaction notes

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