1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10125909, compound

HRID 1376142Notes

Reaction equation

HRID 1376142 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.Cl.[NH2:15][CH:16]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:26].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([NH:15][CH:16]1[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[NH:18][C:17]1=[O:26])=[O:13])=[CH:5]2

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 134994283-Amino-3,4-dihydroquinolin-2(1H)-one--hydrogen chloride (1/1)

Product 1

HCID 10125909HCID 10125909, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloroindole-2-carboxylic acid (196 mg, 1 mmol) was dissolved in DMF (5 mL) containing 3-amino-3,4-dihydroquinolin-2(1H)-one hydrochloride (J. Med. Chem. 28, 1985, 1511–16; 162 mg, 1 mmol), EDCI (192 mg, 1 mmol) and HOBT (135 mg, 1 mmol). The mixture was stirred at ambient temperature for approximately 18 h before being partitioned between water and EtOAc. The organics were washed with water, saturated aqueous NaHCO3, saturated brine and dried over MgSO4; then filtered and evaporated to afford the title compound (212 mg, 66%) as an amorphous white solid.

Workup

  1. custombefore being partitioned between water and EtOAc
  2. washThe organics were washed with water, saturated aqueous NaHCO3, saturated brine
  3. dry with materialdried over MgSO4
  4. filtrationthen filtered
  5. customevaporated

Sources & evidence

ORD record
ord-c485cf78945644e5949ae03c14e6aa3c
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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