Pivaloyl chloride → HCID 58585365, compound

HRID 2252287Notes

Reaction equation

[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[C:27](=[O:28])[N:26]([C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=4)[N:25]=[CH:24][C:23]=3[N:36]3[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH2:37]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>CN(C1C=CN=CC=1)C.ClCCl.N1C=CC=CC=1>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([O:21][C:22]3[C:27](=[O:28])[N:26]([C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=4)[N:25]=[CH:24][C:23]=3[N:36]3[CH2:37][CH2:38][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:40][CH2:41]3)=[CH:19][CH:20]=2)=[CH:11][CH:10]=1)=[O:6]

Participants

Conditions

Temperature: 40 °C

Procedure

0.66 ml of pivaloyl chloride are added dropwise to a suspension of 728 mg (1.18 mmol) of tert-butyl 4-[5-[(4′-hydroxy-1,1′-biphenyl-4-yl)oxy]-1-(4-methyl-phenyl)-6-oxo-1,6-dihydro-4-pyridazinyl]-1-piperazinecarboxylate (Example 46) and a catalytic amount of 4-DMAP in a mixture of dichloromethane (4.0 ml) and pyridine (0.4 ml) at room temperature. The heterogeneous reaction mixture is stirred at about 40° C. overnight. The slightly cloudy suspension is diluted with dichloromethane and washed with 0.2 N hydrochloric acid solution and saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The crude product is purified by chromatography on silica gel.

Workup

washwashed with 0.2 N hydrochloric acid solution and saturated sodium chloride solution
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe crude product is purified by chromatography on silica gel

Sources & evidence

ORD record: ord-deb35b31a1b241de870eb79be7a39602
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320977B2

Reaction notes

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