1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 23289943, compound

HRID 366825Notes

Reaction equation

HRID 366825 reaction equation
C([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([N+:17]([O-:19])=[O:18])[C:13]3[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=3[C:11]=2[CH:10]([CH2:24][Cl:25])[CH2:9]1)=O)(C)(C)C.CCN=C=NCCCN(C)C.Cl.[C:38]([NH:41][C:42]1[CH:43]=[C:44]([CH:50]=[CH:51][CH:52]=1)/[CH:45]=[CH:46]/C(O)=O)(=[O:40])[CH3:39]>CC(N(C)C)=O>[C:38]([NH:41][C:42]1[CH:43]=[C:44]([CH:50]=[CH:51][CH:52]=1)/[CH:45]=[CH:46]/[C:6]([N:8]1[C:16]2[CH:15]=[C:14]([N+:17]([O-:19])=[O:18])[C:13]3[CH:20]=[CH:21][CH:22]=[CH:23][C:12]=3[C:11]=2[CH:10]([CH2:24][Cl:25])[CH2:9]1)=[O:5])(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15023502HCID 15023502, compoundHCID 153804133-(tert-butyloxycarbonyl)-1-chloromethyl-5-nitro-1,2-dihydro-3H-benz[e]indole

Product 1

HCID 23289943HCID 23289943, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Deprotection of 13 (250 mg, 0.69 mmol) as in Example C above and reaction of the product with EDCI.HCl (332 mg, 1.73 mmol), (E)-3-(acetylamino)cinnamic acid (148 mg, 0.72 mmol) and DMA (3 mL) at 20° C. for 3 h, followed by addition of dilute KHCO3, precipitated. This was collected, dissolved in warm EtOAc (180 mL) and filtered through a column of silica gel. Solvent concentration followed by addition of i-Pr2O precipitated the crude product which was recrystallised from EtOAc/i-Pr2O to give 14k (232 mg, 75%), mp 214-216° C. 1H NMR [(CD3)2SO] δ 10.07 (s, 1 H, NH), 9.22 (s, 1 H, H-4), 8.33 (dd, J=7.8, 1.9 Hz, 1 H, H-6), 8.19 (dd, J=7.3, 1.6 Hz, 1 H, H-9), 7.88 (s, 1 H, H-2'), 7.78-7.63 (m, 3 H, H-7,8,4'), 7.68 (d, J=15.3 Hz, 1 H, PhCH=CH), 7.55 (d, J=7.8 Hz, 1 H, H-6'), 7.39 (t, J=7.9 Hz, 1 H, H-5'), 7.14 (d, J=15.4 Hz, 1 H, PhCH=CH), 4.72-4.55 (m, 3 H, H-1,2), 4.12-4.05 (m, 2 H, CH2Cl), 2.08 (s, 3 H, CH3). Anal. Calculated for C24H20ClN3O4 : C, 64.1; H, 4.5; N, 9.2; Cl, 7.9. Found: C, 64.3; H, 4.4; N, 9.3; Cl, 7.8%.

Workup

  1. customprecipitated
  2. customThis was collected
  3. dissolutiondissolved in warm EtOAc (180 mL)
  4. filtrationfiltered through a column of silica gel
  5. concentrationSolvent concentration
  6. additionfollowed by addition of i-Pr2O
  7. customprecipitated the crude product which
  8. customwas recrystallised from EtOAc/i-Pr2O

Sources & evidence

ORD record
ord-fccd8cf1688747cfbabfb0d0c9fcdd44
Source dataset
uspto-grants-2000_10
Patent number
US06130237

Reaction notes

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