Triethylamine → (S)-3-(1-(2-chloro-3-nitropyridin-4-ylamino)ethyl)-2-phenyl-8-(trifluoromethyl)isoquinolin-1(2H)-one

HRID 869472Notes

Reaction equation

HRID 869472 reaction equation
[NH2:1][C@H:2]([C:4]1[N:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6](=[O:18])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[C:14]([F:17])([F:16])[F:15])[CH3:3].[Cl:25][C:26]1[C:31]([N+:32]([O-:34])=[O:33])=[C:30](Cl)[CH:29]=[CH:28][N:27]=1.C(N(CC)CC)C>CCO>[Cl:25][C:26]1[C:31]([N+:32]([O-:34])=[O:33])=[C:30]([NH:1][C@H:2]([C:4]2[N:5]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:6](=[O:18])[C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][C:8]=3[C:14]([F:15])([F:16])[F:17])[CH3:3])[CH:29]=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 105357732,4-Dichloro-3-nitropyridineHCID 71232651(S)-3-(1-aminoethyl)-2-phenyl-8-(trifluoromethyl)isoquinolin-1(2H)-one

Product 1

HCID 86676288(S)-3-(1-(2-chloro-3-nitropyridin-4-ylamino)ethyl)-2-phenyl-8-(trifluoromethyl)isoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of (S)-3-(1-aminoethyl)-2-phenyl-8-(trifluoromethyl)isoquinolin-1(2H)-one III-1 (1.0 g, 3.0 mmol, 1.0 eq) and 2,4-dichloro-3-nitropyridine (578 mg, 3.0 mmol, 1.0 eq) in EtOH (10 mL), triethylamine (608 mg, 6.0 mmol, 2.0 eq) was added and the resulting mixture was stirred at reflux overnight. The mixture was allowed to cool to RT and then concentrated in vacuo. The resultant residue was purified by flash column chromatography on silica gel (1% MeOH-DCM) to afford the product, (S)-3-(1-(2-chloro-3-nitropyridin-4-ylamino)ethyl)-2-phenyl-8-(trifluoromethyl)isoquinolin-1(2H)-one III-33.

Workup

  1. additionwas added
  2. temperatureat reflux overnight
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue was purified by flash column chromatography on silica gel (1% MeOH-DCM)

Sources & evidence

ORD record
ord-3a1f246d135e483e99c6178c80c41e27
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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