Hydrochloric Acid → HCID 67994842, compound

HRID 2361424Notes

Reaction equation

HRID 2361424 reaction equation
[CH3:1][C:2]1[C:7]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:19]1[CH:27]=[CH:26][C:25]([C:28]([NH2:30])=[O:29])=[C:24]2[C:20]=1[C:21]1[CH2:34][N:33](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:32][CH2:31][C:22]=1[NH:23]2.CCOC(C)=O.Cl>CO>[CH3:1][C:2]1[C:7]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:19]1[CH:27]=[CH:26][C:25]([C:28]([NH2:30])=[O:29])=[C:24]2[C:20]=1[C:21]1[CH2:34][NH:33][CH2:32][CH2:31][C:22]=1[NH:23]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 67994678HCID 67994678, compound

Product 1

HCID 67994842HCID 67994842, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 9-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-2-trityl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-6-carboxamide (248.5 mg, 0.359 mmol) in methanol (4 mL) was treated with EtOAc (less than 1 mL) to form a clear solution. This was treated with 1 M aqueous HCl (3 mL), forming a cloudy mixture which was stirred at room temperature. After 30 min, the mixture was concentrated under vacuum, treated with NaHCO3 (aq) and EtOAc and stirred at room temperature for about 1 h. The precipitate was collected by filtration, washed with water, then with EtOAc, and dried under vacuum to provide the desired product as a white solid (145 mg, 90% yield).

Workup

  1. customto form a clear solution
  2. customforming a cloudy mixture which
  3. concentrationthe mixture was concentrated under vacuum
  4. additiontreated with NaHCO3 (aq) and EtOAc
  5. stirringstirred at room temperature for about 1 h
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. dry with materialwith EtOAc, and dried under vacuum

Sources & evidence

ORD record
ord-feac365f08bb4682af1650f797790e05
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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