1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58788458, compound

HRID 1376159Notes

Reaction equation

HRID 1376159 reaction equation
[CH:1]1C=CC2N(O)N=N[C:5]=2[CH:6]=1.ClC1C=C2C(=CC=1)NC([C:21](O)=[O:22])=C2.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.[Cl:44][C:45]1[CH:46]=[C:47]2[C:51](=[CH:52][CH:53]=1)[NH:50][C:49]([C:54]([NH:56][CH:57]1[CH2:66][C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[N:59]([CH2:67][C:68](=[O:75])NC3SC=NN=3)[C:58]1=[O:76])=[O:55])=[CH:48]2>C(Cl)Cl.CCOC(C)=O>[Cl:44][C:45]1[CH:46]=[C:47]2[C:51](=[CH:52][CH:53]=1)[NH:50][C:49]([C:54]([NH:56][CH:57]1[CH2:66][C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[N:59]([CH2:67][C@@H:68]3[CH2:21][O:22][C:6]([CH3:5])([CH3:1])[O:75]3)[C:58]1=[O:76])=[O:55])=[CH:48]2

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 10288845HCID 10288845, compound

Product 1

HCID 58788458HCID 58788458, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

HOBT (209 mg, 1.55 mmol), 5-chloroindole-2-carboxylic acid (303 mg, 1.55 mmol), DIPEA (0.27 mL, 1.55 mmol) and then EDCI (370 mg, 1.94 mmol) were added to a solution of 3-amino-1-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-3,4-dihydroquinolin-2(1H)-one (Method 8, 428 mg, 1.55 mmol) in DCM (10 mL). The reaction was stirred for 18 h at ambient temperature, diluted with EtOAc (20 mL), washed with 1 N NaOH (15 mL), 0.1 N HCl (15 mL), saturated aqueous NaHCO3 solution (15 mL), dried (Na2SO4) and the volatiles removed under reduced pressure to give the title compound (684 mg, 97%) as a pale yellow solid.

Workup

  1. washwashed with 1 N NaOH (15 mL), 0.1 N HCl (15 mL), saturated aqueous NaHCO3 solution (15 mL)
  2. dry with materialdried (Na2SO4)
  3. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-a7cb0f5008e54b6697c53b93d24eb226
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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