1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67200176, compound

HRID 547560Notes

Reaction equation

HRID 547560 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N:19]([CH3:21])[CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:22]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](O)=[O:29])(=[O:24])[CH3:23].CCN=C=NCCCN(C)C.C(Cl)[Cl:46].CO>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl-:46].[C:22]([C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N:19]([CH3:21])[CH3:20])[CH:17]=3)[NH+:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1)=[O:29])(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2203243-Acetylbenzoic acidHCID 21226129Dichloromethane methanolHCID 59457979HCID 59457979, compound

Product 1

HCID 67200176HCID 67200176, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of N4-(4-Aminophenyl)-N6,N6-dimethyl-4,6-quinolinediamine (181 mg, 0.58 mmol), 3-acetylbenzoic acid (M1) (97 mg, 0.58 mmol) and EDCI (220 mg, 0.1.16 mmol) in DMF (5 mL) was stirred at 20° C. for 5 min. Then DMAP (140 mg, 1.16 mmol) was added and the reaction mixture was stirred at 20° C. for 24 h. The solvent was removed under reduced pressure and residue was stirred in aqueous NaHCO3 for 1 h. The resulting precipitate was filtered and purified by chromatography in SiO2 eluting with a gradient (0-7.5%) of MeOH/DCM to give M2 (113 mg, 42%); mp (DCM/MeOH)>280° C.; 1HNMR [(CD3)2SO] δ14.02 (br, 1 H, N+H), 10.66 (s, 1 H, NH), 10.31 (s, 1 H, NH), 8.53 (t, J=1.6 Hz, 1 H, ArH), 8.28 (d, J=6.7 Hz, 1 H, ArH), 8.24 (td, J=8.1, 1.5 Hz, 1 H, ArH), 8.19 (td, J=7.8, 2.8 Hz, 1 H, ArH), 8.00 (d, J=6.8 Hz, 2 H, ArH), 7.87 (d, J=9.4 Hz, 1 H, ArH), 7.78 (t, J=7.8 Hz, 1 H, ArH), 7.64 (dd, J=9.4, 2.6 Hz, 1 H, ArH), 7.51 (d, J=2.5 Hz, 1 H, ArH), 7.47 (d, J=8.8 Hz, 2 H, ArH), 6.69 (d, J=6.7 Hz, 1 H, ArH), 3.09 [s, 6 H, (NCH3)2], 2.68 (s, 3 H, COCH3); APCI+ve 425.

Workup

  1. stirringthe reaction mixture was stirred at 20° C. for 24 h
  2. customThe solvent was removed under reduced pressure and residue
  3. stirringwas stirred in aqueous NaHCO3 for 1 h
  4. filtrationThe resulting precipitate was filtered
  5. custompurified by chromatography in SiO2 eluting with a gradient (0-7.5%) of MeOH/DCM
  6. customto give M2 (113 mg, 42%)

Sources & evidence

ORD record
ord-89781c13ec794865ab32c8d2ba494086
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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