1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67199240, compound

HRID 1711370Notes

Reaction equation

HRID 1711370 reaction equation
[ClH:1].[NH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)[CH:6]=[C:5]([CH3:19])[N:4]=1.CCN=C=NCCCN(C)C.Cl.[NH2:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]2[C:49]3[C:44](=[CH:45][CH:46]=[C:47]([N:50]([CH3:52])[CH3:51])[CH:48]=3)[N:43]=[CH:42][CH:41]=2)=[CH:35][CH:34]=1.CO.CCOC(C)=O>CN(C1C=CN=CC=1)C.CN1C(=O)CCC1.O>[ClH:1].[ClH:1].[NH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([NH:32][C:33]3[CH:34]=[CH:35][C:36]([NH:39][C:40]4[C:49]5[C:44](=[CH:45][CH:46]=[C:47]([N:50]([CH3:52])[CH3:51])[CH:48]=5)[N:43]=[CH:42][CH:41]=4)=[CH:37][CH:38]=3)=[O:16])=[CH:17][CH:18]=2)[CH:6]=[C:5]([CH3:19])[N:4]=1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21584119Ethylacetate methanolHCID 59457979HCID 59457979, compoundHCID 67202054HCID 67202054, compound

Product 1

HCID 67199240HCID 67199240, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
20 °C

Procedure

Compound D2 (111 mg, 0.4 mmol), EDCl (155 mg, 0.72 mmol) and DMAP (174 mg, 1.44 mmol) in N-methyl pyrrolidinone (5 mL) was stirred 5 min at 20° C. N4-(4-Aminophenyl)-N6,N6-dimethyl-4,6-quinolinediamine (100 mg, 0.36 mmol) was then added and the reaction mixture was stirred at 20° C. for 20 h. The reaction mixture was diluted with water and stirred. The resulting precipitate was filtered washed with water and air dried. This solid was dissolved in hot MeOH, boiled with charcoal and filtered through a pad of celite. The filtrate was evaporated to dryness and the resulting residue was dissolved in MeOH (10 mL), 1.25 M HCl in MeOH (1 mL) was added and stirred 10 min. The solvent was evaporated and the residue was recrystallized from MeOH/EtOAc to give Cpd. HH (135 mg, 65%) as a yellow solid; m.p. (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ 14.10 (br, 1H, N+H), 12.75 (br, 1H, N+H), 10.85 (br, 1H, NH), 10.45 (s, 1H, NH), 10.40 (s, 1H, NH), 8.27 (d, J=6.8 Hz, 1H, ArH), 8.08-7.99 (m, 6H, ArH), 7.88 (d, J=9.4 Hz, 1H, ArH), 7.65 (dd, J=9.4, 2.5 Hz, 1H, ArH), 7.54 (d, J=2.4 Hz, 1H, ArH), 7.45 (d, J=8.9 Hz, 2H, ArH), 6.67 (d, J=6.8 Hz, 1H, ArH), 6.27 (s, 1H, ArH), 3.12 [s, 6H, N(CH3)2], 2.32 (s, 3H, CH3); mass APCl+505.

Workup

  1. stirringstirred
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water and air
  4. customdried
  5. dissolutionThis solid was dissolved in hot MeOH
  6. filtrationfiltered through a pad of celite
  7. customThe filtrate was evaporated to dryness
  8. dissolutionthe resulting residue was dissolved in MeOH (10 mL)
  9. addition1.25 M HCl in MeOH (1 mL) was added
  10. stirringstirred 10 min
  11. customThe solvent was evaporated
  12. customthe residue was recrystallized from MeOH/EtOAc
  13. customto give Cpd

Sources & evidence

ORD record
ord-ec74efb950e74a308f7806dc231160be
Source dataset
uspto-grants-2010_09
Patent number
US07790746B2

Reaction notes

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