Hydrochloric Acid → 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)amino]benzoic acid hydrochloride

HRID 1877522Notes

Reaction equation

[ClH:1].[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[CH2:43][CH:42]6[N:44]([CH3:45])[CH:39]([CH2:40][CH2:41]6)[CH2:38]5)[CH:24]=4)[C:14]=3[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)#[N:3]>O1CCOCC1>[ClH:1].[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[CH2:43][CH:42]6[N:44]([CH3:45])[CH:39]([CH2:40][CH2:41]6)[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

3.49 ml of 1N hydrochloric acid are added to a solution of 340 mg of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)amino]benzoate in 6 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 trituration with diisopropyl ether, so as to give 330 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)amino]benzoic acid hydrochloride 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 trituration with diisopropyl ether

Sources & evidence

ORD record: ord-94401c0ca65d45759e533c20ac3af784
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309721B2

Reaction notes

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