1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67199240, compound

HRID 547551Notes

Reaction equation

HRID 547551 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.[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([NH:38][C:39]2[C:48]3[C:43](=[CH:44][CH:45]=[C:46]([N:49]([CH3:51])[CH3:50])[CH:47]=3)[N:42]=[CH:41][CH:40]=2)=[CH:34][CH:33]=1.CO.CCOC(C)=O>CN(C1C=CN=CC=1)C.CN1CCCC1=O.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:31][C:32]3[CH:33]=[CH:34][C:35]([NH:38][C:39]4[C:48]5[C:43](=[CH:44][CH:45]=[C:46]([N:49]([CH3:51])[CH3:50])[CH:47]=5)[N:42]=[CH:41][CH:40]=4)=[CH:36][CH:37]=3)=[O:16])=[CH:17][CH:18]=2)[CH:6]=[C:5]([CH3:19])[N:4]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 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), EDCI (155 mg, 0.72 mmol) and DMAP (174 mg, 1.44 mmol) in N-methylpyrrolidinone (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 recrytallized from MeOH/EtOAc to give Cpd. HH (135 mg, 65%) as a yellow solid; m.p. (MeOH/EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ14.10 (br, 1 H, N+H), 12.75 (br, 1 H, N+H), 10.85 (br, 1 H, NH), 10.45 (s, 1 H, NH), 10.40 (s, 1 H, NH), 8.27 (d, J=6.8 Hz, 1 H, ArH), 8.08-7.99 (m, 6 H, ArH), 7.88 (d, J=9.4 Hz, 1 H, ArH), 7.65 (dd, J=9.4, 2.5 Hz, 1 H, ArH), 7.54 (d, J=2.4 Hz, 1 H, ArH), 7.45 (d, J=8.9 Hz, 2 H, ArH), 6.67 (d, J=6.8 Hz, 1 H, ArH), 6.27 (s, 1 H, ArH), 3.12 [s, 6 H, N(CH3)2], 2.32 (s, 3 H, CH3); mass APCI+ 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. customto give Cpd

Sources & evidence

ORD record
ord-286c42d5ba684cf88bdbf48b94803aa0
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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