Tert-Butylamine → N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide

HRID 1962853Notes

Reaction equation

HRID 1962853 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:18][CH3:19])[C:15]([OH:17])=O)=[CH:8][CH:7]=2)#[CH:2].[C:20]([NH2:24])([CH3:23])([CH3:22])[CH3:21].Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>[C:20]([NH:24][C:15](=[O:17])[CH:14]([O:13][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:12]2)[S:18][CH3:19])([CH3:23])([CH3:22])[CH3:21]

Participants

9

Reactant 4

HCID 6385Tert-ButylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59565474(3-Ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid

Product 1

HCID 59565325N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide

Reagents, catalysts & solvents 4

HCID 181649HOAtCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3-Ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (1.1 g), N-tert-Butyl amine (0.467 ml), 1-hydroxy-7-azabenzotriazole (HOAT) (0.602 mg), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCl) (849 mg) and triethylamine (0.84 ml) in dry N,N-dimethylformamide (20 ml) were stirred at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and poured on 60 ml aq. sat. sodium hydrogen carbonate. The water phase was extracted with 3×150 ml ethyl acetate. All organic layers were combined, dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (heptane/ethyl acetate 13:7) to give N-tert-Butyl-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (1.11 g) as yellowish solid.

Workup

  1. extractionThe water phase was extracted with 3×150 ml ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (heptane/ethyl acetate 13:7)

Sources & evidence

ORD record
ord-b69284d9e63246f588a556c8d1ce4bb4
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

Loading…