Water → HCID 178520512, compound

HRID 1634581Notes

Reaction equation

HRID 1634581 reaction equation
[CH:1]1[N:5]=[CH:4][NH:3][C:2]=1/[CH:6]=[CH:7]/[C:8]([OH:10])=O.Cl.CN(C)CCCN=C=NCC.OC1C2N=NNC=2C=CC=1.[Cl:33][C:34]1[CH:35]=[CH:36][C:37]2[CH:47]([N:48]3[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]3)[C:42]3=[N:43][CH:44]=[CH:45][CH:46]=[C:41]3[CH2:40][CH2:39][C:38]=2[CH:54]=1.O>CN(C)C=O>[Cl:33][C:34]1[CH:35]=[CH:36][C:37]2[CH:47]([N:48]3[CH2:49][CH2:50][N:51]([C:8](=[O:10])/[CH:7]=[CH:6]/[C:2]4[N:3]=[CH:4][NH:5][CH:1]=4)[CH2:52][CH2:53]3)[C:42]3=[N:43][CH:44]=[CH:45][CH:46]=[C:41]3[CH2:40][CH2:39][C:38]=2[CH:54]=1

Participants

7

Reactant 5

HCID 962WaterHCID 736715trans-Urocanic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5255691HCID 5255691, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 178520512HCID 178520512, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of urocanic acid (1.38 g; 10.0 mmol) (from Aldrich Chemicals) in N,N-dimethylformamide (175 mL) under an inert atmosphere, was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.92 g; 10.0 mmol) and hydroxybenzotriazole (1.08 g; 8 mmol). The resultant mixture was warmed to 40° C. and stirring continued until all solids dissolved (˜10 min.). To the resultant solution was added 8-chloro-6,11-dihydro-11-(1-piperazinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (8) (2.51 g; 8.0 mmol), and the resultant solution was allowed to stir at room temperature for 18.5 h. Then water (250 microliters; 13.9 mmol) was added, and the solution was stirred briefly before concentrating under reduced pressure. The residual oil was partitioned between dichloromethane (100 mL) and water (100 mL). The organic extract was dried by filtration through anhydrous magnesium sulfate and solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane-methanol-concentrated ammonium hydroxide (90:9:0.5), to obtain the title compound as a yellow powder that decomposed to a frothy gum at 160° C. SIMS: 434 (MH+; 50%).

Workup

  1. dissolutiondissolved (˜10 min.)
  2. stirringto stir at room temperature for 18.5 h
  3. stirringthe solution was stirred briefly
  4. concentrationbefore concentrating under reduced pressure
  5. customThe residual oil was partitioned between dichloromethane (100 mL) and water (100 mL)
  6. extractionThe organic extract
  7. dry with materialwas dried by filtration through anhydrous magnesium sulfate and solvent
  8. customremoved under reduced pressure
  9. customThe residue was chromatographed on silica gel
  10. washeluting with dichloromethane-methanol-concentrated ammonium hydroxide (90:9:0.5)

Sources & evidence

ORD record
ord-edd6b1533ac5408aaccaaf2662635505
Source dataset
uspto-grants-2003_01
Patent number
US06506756B2

Reaction notes

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