Hydrochloric Acid → 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]benzoic acid

HRID 1877514Notes

Reaction equation

Cl.[C:2]([C:4]1[N:9]=[CH:8][C:7]([C:10]2[C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]([C:23]4[CH:35]=[CH:34][C:26]([C:27]([O:29]C(C)(C)C)=[O:28])=[C:25]([NH:36][CH:37]5[CH2:42][C:41]([CH3:44])([CH3:43])[N:40]([CH3:45])[C:39]([CH3:47])([CH3:46])[CH2:38]5)[CH:24]=4)[C:14]=3[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)#[N:3]>O1CCOCC1>[C:2]([C:4]1[N:9]=[CH:8][C:7]([C:10]2[C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]([C:23]4[CH:35]=[CH:34][C:26]([C:27]([OH:29])=[O:28])=[C:25]([NH:36][CH:37]5[CH2:42][C:41]([CH3:43])([CH3:44])[N:40]([CH3:45])[C:39]([CH3:47])([CH3:46])[CH2:38]5)[CH:24]=4)[C:14]=3[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)#[N:3]

Participants

Conditions

Temperature: 100 °C

Procedure

7.7 ml of 1N hydrochloric acid are added to a solution of 0.79 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]benzoate in 5 ml of dioxane. The reaction mixture is heated at 100° C. in a microwave for 2 hours and then concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a mixture of dichloromethane and methanol (95/5 by volume), so as to give 280 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]benzoic acid in the form of a pale yellow powder, the characteristics of which are the following:

Workup

concentrationconcentrated under reduced pressure
customThe residue is purified by silica gel chromatography, elution
additionbeing carried out with a mixture of dichloromethane and methanol (95/5 by volume)

Sources & evidence

ORD record: ord-61e4c5bf4cfb4d988c57f703c9043038
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309721B2

Reaction notes

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