Triethylamine → HCID 86698492, compound

HRID 1773483Notes

Reaction equation

HRID 1773483 reaction equation
[NH2:1][C@H:2]([C:4]1[N:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6](=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:14])[CH3:3].C(N(CC)CC)C.Cl.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[N:33][CH:32]=1>CN(C)C(=O)C.C1COCC1>[Cl:14][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[C:6](=[O:15])[N:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:4]([C@@H:2]([NH:1][C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[N:33][CH:32]=1)[CH3:3])=[CH:13]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 66607319(S)-3-(1-aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one

Product 1

HCID 86698492HCID 86698492, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a mixture of (S)-3-(1-aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one (1) (50 mg, 0.17 mmol) in a mixture of N,N-dimethylacetamide (1 mL) and THF (3 mL), triethylamine (0.07 mL, 0.50 mmol) and nicotinoyl chloride hydrochloride (32 mg, 0.18 mmol) were added and the resulting mixture was stirred at RT for 30 min. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and purified by ISCO column chromatography (silica gel cartridge, 0-10% MeOH-DCM) to afford the product, (S)-N-(1-(8-chloro-1-oxo-2-phenyl-1,2-dihydroisoquinolin-3-yl)ethyl)nicotinamide (compound 51). ESI-MS m/z: 404.0 [M+H]+.

Workup

  1. additionwere added
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. custompurified by ISCO column chromatography (silica gel cartridge, 0-10% MeOH-DCM)

Sources & evidence

ORD record
ord-47b76f90372a41ecb2f6088d2ae52096
Source dataset
uspto-grants-2016_02
Patent number
US09255108B2

Reaction notes

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