Ethylenediamine → 6-(4,5-Dihydro-1H-imidazol-2-yl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxamide

HRID 62341Notes

Reaction equation

HRID 62341 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:16]([NH:18][CH2:19][C:20]2[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=2[CH3:26])=[O:17])[C:6]2[C:7]([CH3:15])=[CH:8][N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=2[CH:11]=1)#[N:2].[CH2:29](N)[CH2:30][NH2:31]>P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S>[NH:2]1[CH2:29][CH2:30][N:31]=[C:1]1[C:3]1[CH:4]=[C:5]([C:16]([NH:18][CH2:19][C:20]2[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=2[CH3:26])=[O:17])[C:6]2[C:7]([CH3:15])=[CH:8][N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 67467470HCID 67467470, compound

Product 1

HCID 674685726-(4,5-Dihydro-1H-imidazol-2-yl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxamideYield 86.7%

Reagents, catalysts & solvents 1

HCID 14817Phosphorus sulfide (P2S5)Catalyst

Conditions

Temperature
120 °C

Procedure

To a 10-mL microwave tube were added 6-cyano-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-indole-4-carboxamide (33 mg, 0.088 mmol), ethylenediamine (1 mL, 14.81 mmol), and phosphorus pentasulfide (0.585 mg, 2.63 μmol), and the mixture was degassed for 5 min. The tube was sealed and the mixture was heated at 120° C. in a microwave. The mixture was concentrated and the residue was purified using reverse-phase HPLC under acidic conditions to give 32 mg of product as off-white solid. 1H NMR (400 MHz, DMSO-d6) ppm 1.46 (m, 6H), 2.11 (s, 3H), 2.17 (s, 3H), 2.24 (s, 3H), 4.35 (d, J=5.05 Hz, 2H), 4.75 (quin, J=6.69 Hz, 1H), 5.87 (s, 1H), 7.49-7.60 (m, 2H), 8.16-8.26 (m, 2H), 8.39 (s, 1H). MS: (M+H)+=419.9.

Workup

  1. customthe mixture was degassed for 5 min
  2. customThe tube was sealed
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified

Sources & evidence

ORD record
ord-7db28ff838e241ba92759dd62ea81e3b
Source dataset
uspto-grants-2016_09
Patent number
US09446041B2

Reaction notes

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