Hydrochloric Acid → HCID 66835233, compound

HRID 61898Notes

Reaction equation

HRID 61898 reaction equation
[CH3:1][C:2]1([CH3:31])[O:6][C@@H:5]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[C:24](=[O:25])[C:23]4[C:22]5[C:17](=[CH:18][C:19]([C:26]#[N:27])=[CH:20][CH:21]=5)[NH:16][C:15]=4[C:14]([CH3:29])([CH3:28])[C:13]=3[CH:30]=2)[CH2:4][O:3]1.[Cl-].[NH4+].[N-:34]=[N+:35]=[N-:36].[Na+].Cl>CN(C=O)C>[CH3:1][C:2]1([CH3:31])[O:6][C@@H:5]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]3[C:24](=[O:25])[C:23]4[C:22]5[C:17](=[CH:18][C:19]([C:26]6[N:34]=[N:35][NH:36][N:27]=6)=[CH:20][CH:21]=5)[NH:16][C:15]=4[C:14]([CH3:29])([CH3:28])[C:13]=3[CH:30]=2)[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium Azide2×HCID 66834868HCID 66834868, compound

Product 1

HCID 66835233HCID 66835233, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

8-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (20.0 mg, 0.048 mmol), ammonium chloride (1.28 mg, 0.024 mmol) and NaN3 (6.24 mg, 0.096 mmol) were dissolved in DMF, and the mixture was stirred at 120° C. for 14 hrs. NaN3 (6.24 mg, 0.096 mmol) was further added to the mixture, which was then stirred at 120° C. for 30 hrs. The reaction solution was added with 1 N aqueous solution of hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and concentrated under reduced pressure. The resultant solid obtained after concentration was washed with hexane:ethyl acetate=1:1 to obtain 8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-3-(2H-tetrazol-5-yl)-5,6-dihydro-benzo[b]carbazol-11-one as a white solid.

Workup

  1. stirringwas then stirred at 120° C. for 30 hrs
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant solid obtained
  6. concentrationafter concentration
  7. washwas washed with hexane

Sources & evidence

ORD record
ord-a97a80a548b34a94b5e650858e3d0c8e
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

Loading…