1,2-Dichloroethane → HCID 70980905, compound

HRID 572356Notes

Reaction equation

HRID 572356 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][N:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2].[CH3:33][N:34]([CH3:39])[CH2:35][CH2:36][CH2:37]O.C(Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([O:20][CH2:37][CH2:36][CH2:35][N:34]([CH3:39])[CH3:33])=[O:19])=[CH:16][N:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][N:25]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 766463-(Dimethylamino)-1-propanolHCID 70979776HCID 70979776, compound

Product 1

HCID 70980905HCID 70980905, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)nicotinic acid (for a preparation see Intermediate 7) (100 mg, 0.234 mmol) in DMF (5 mL) were added 3-(dimethylamino)-1-propanol (121 mg, 1.170 mmol), EDC (90 mg, 0.468 mmol) and DMAP (2.86 mg, 0.023 mmol). The resulting mixture was stirred at room temperature overnight, the reaction mixture was concentrated in vacuo, dissolved in a 1:1 MeOH/DMSO mixture and purified by MDAP (HpH). The appropriate fractions were combined and concentrated under reduced pressure to give 3-(dimethylamino)propyl 6-((2S,4R)-1-acetyl-4-((5-cyanopyridin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)nicotinate (23 mg, 19%) as a colourless oil. LCMS (Formate, 2 min), Rt=0.70 min, MH+=513.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in a 1:1 MeOH/DMSO mixture
  3. custompurified by MDAP (HpH)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37a0afa4cb4043ee8949b1ab8a49cc31
Source dataset
uspto-grants-2015_05
Patent number
US09029395B2

Reaction notes

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