1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide

HRID 1376161Notes

Reaction equation

HRID 1376161 reaction equation
C1C=CC2N(O)N=NC=2C=1.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:21]([OH:23])=O)=[CH:15]2.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.[NH2:44][CH:45]1[CH2:54][C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]([CH2:55][C:56]#[N:57])[C:46]1=[O:58]>C(Cl)Cl.CCOC(C)=O>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:21]([NH:44][CH:45]1[CH2:54][C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:47]([CH2:55][C:56]#[N:57])[C:46]1=[O:58])=[O:23])=[CH:15]2

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 21906832(3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetonitrile

Product 1

HCID 100452425-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamideYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

HOBT (168 mg, 1.24 mmol), 5-chloroindole-2-carboxylic acid (243 mg, 1.24 mmol), DIPEA (0.22 mL, 1.24 mmol) and then EDCI (296 mg, 1.55 mmol) were added to a solution of (3-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)acetonitrile (Method 12, 250 mg, 1.24 mmol) in DCM (10 mL). The reaction was stirred for 18 h at ambient temperature, diluted with EtOAc (15 mL), washed with 1 N NaOH (15 mL), 1 N HCl (15 mL), saturated aqueous NaHCO3 solution (15 mL), dried (MgSO4) and the volatiles removed under reduced pressure to give the title compound (366 mg, 78%) as a tan solid.

Workup

  1. washwashed with 1 N NaOH (15 mL), 1 N HCl (15 mL), saturated aqueous NaHCO3 solution (15 mL)
  2. dry with materialdried (MgSO4)
  3. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-3ad868c3cfcc466b825a720c35ad06ba
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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