Hydrochloric Acid → HCID 67308714, compound

HRID 1877508Notes

Reaction equation

HRID 1877508 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][CH2:37][CH2:38][C:39]([OH:42])([CH3:41])[CH3:40])[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][CH2:37][CH2:38][C:39]([OH:42])([CH3:40])[CH3:41])[CH:24]=4)[C:14]=3[CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)#[N:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67308214HCID 67308214, compound

Product 1

HCID 67308714HCID 67308714, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1.6 ml of 1N hydrochloric acid are added to a solution of 0.15 g of 2-methylpropan-2-yl 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxy-3-methylbutyl)amino]benzoate in 8 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 (97/3 by volume), so as to give 20 mg of 4-[4-(6-cyanopyridin-3-yl)-9H-carbazol-9-yl]-2-[(3-hydroxy-3-methylbutyl)amino]benzoic acid in the form of a pale yellow powder, the characteristics of which are the following:

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified by silica gel chromatography, elution
  3. additionbeing carried out with a mixture of dichloromethane and methanol (97/3 by volume)

Sources & evidence

ORD record
ord-7df4a876c2864dc38af4a0bd0b220071
Source dataset
uspto-grants-2012_11
Patent number
US08309721B2

Reaction notes

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