Hydrochloric Acid → HCID 9909321, compound

HRID 324995Notes

Reaction equation

HRID 324995 reaction equation
[CH3:1][N:2]([CH3:29])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:16]([OH:18])=O)[CH:12]=3)[N:7]([Si](C(C)C)(C(C)C)C(C)C)[C:6]=2[CH2:5][CH2:4]1.[ClH:30].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:52][C:53]1[CH:58]=[CH:57][N:56]=[CH:55][CH:54]=1.[N-]=C=O.Cl>CN(C)C=O.O1CCCC1.ClCCl>[ClH:30].[ClH:30].[N:56]1[CH:57]=[CH:58][C:53]([NH:52][C:16]([C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6]2[CH2:5][CH2:4][CH:3]([N:2]([CH3:29])[CH3:1])[CH2:15][C:14]3=2)=[O:18])=[CH:54][CH:55]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 17274-Aminopyridine2×HCID 757711-HydroxybenzotriazoleHCID 105034IsocyanateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15512575HCID 15512575, compound

Product 1

HCID 9909321HCID 9909321, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.41 gm (1.0 mMol) 3-dimethylamino-9-triisopropylsilyl-1,2,3,4-tetrahydro-9H-carbazole-6-carboxylic acid, 0.77 gm (4.0 mMol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.54 gm (4.0 mMol) 1-hydroxybenzotriazole, and 0.38 gm (4.0 mMol) 4-aminopyridine in 10 mL dimethylformamide and 50 mL tetrahydrofuran were stirred together at room temperature for 3 days. Polystyrene bound isocyanate resin was added to the reaction mixture which was stirred at 40° C. for 6 hours to scavenge excess 4-aminopyridine. The reaction mixture was filtered, concentrated under reduced pressure and the residue subjected to preparative centrifugal thin layer chromatography (PCTLC), eluting with chloroform containing 5% methanol and 0.5% ammonium hydroxide. Fractions containing the desilylated product were combined and concentrated under reduced pressure to provide a yellow oil. This oil was dissolved in dichloromethane and treated with ethanolic hydrogen chloride. The resulting mixture was concentrated under reduced pressure to provide 0.22 gm (54%) of the title compound as a tan solid.

Workup

  1. additionwas added to the reaction mixture which
  2. stirringwas stirred at 40° C. for 6 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. washeluting with chloroform containing 5% methanol and 0.5% ammonium hydroxide
  6. additionFractions containing the desilylated product
  7. concentrationconcentrated under reduced pressure
  8. customto provide a yellow oil
  9. concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ec200fbfbc124cb19f297f7ea9a13432
Source dataset
uspto-grants-2001_04
Patent number
US06221884B1

Reaction notes

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