1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 70095412, compound

HRID 868914Notes

Reaction equation

HRID 868914 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[CH2:11][CH2:12][C:13]([OH:15])=[O:14].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:37]1[C:46]2[C:41](=[C:42]([NH2:48])[C:43]([NH2:47])=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1>C(Cl)Cl>[NH2:48][C:42]1[C:43]([NH:47][C:13](=[O:15])[CH2:12][CH2:11][C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[CH:44][CH:45]=[C:46]2[C:41]=1[CH:40]=[CH:39][CH:38]=[N:37]2.[NH2:47][C:43]1[C:42]([NH:48][C:13](=[O:14])[CH2:12][CH2:11][C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[C:41]2[C:46](=[CH:45][CH:44]=1)[N:37]=[CH:38][CH:39]=[CH:40]2

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2925043-(quinoxalin-2-yl)propanoic acidHCID 426874Quinoline-5,6-diamine

Product 2

HCID 70095412HCID 70095412, compoundHCID 70097400HCID 70097400, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(quinoxalin-2-yl)propanoic acid (550 mg, 2.7 mmol) in DCM (30 mL) was added HOBt (550 mg, 4 mmol) and EDCI (780 mg, 4 mmol). After stirring for 30 minutes, quinoline-5,6-diamine (430 mg, 2.7 mmol) was added and the reaction was stirred for 3 hours. The mixture was washed with water (10 mL) and extracted with DCM (30 mL×3). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford a yellow mixture which was purified by reverse phase chromatography. N-(5-Aminoquinolin-6-yl)-3-(quinoxalin-2-yl)propanamide (180 mg) and N-(6-aminoquinolin-5-yl)-3-(quinoxalin-2-yl)propanamide (80 mg) were isolated. MS (ESI) m/z 343 (M+H+).

Workup

  1. stirringthe reaction was stirred for 3 hours
  2. washThe mixture was washed with water (10 mL)
  3. extractionextracted with DCM (30 mL×3)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a yellow mixture which
  8. customwas purified by reverse phase chromatography

Sources & evidence

ORD record
ord-7ebc2facb2034a4ea8a56b5956e90d7e
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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