Hydrochloric Acid → HCID 59565266, compound

HRID 1962854Notes

Reaction equation

HRID 1962854 reaction equation
[NH2:1][C:2]([CH3:7])([CH2:5][F:6])[C:3]#[N:4].ON1C2N=CC=CC=2N=N1.CN(C)CCCN=C=NCC.Cl.[C:30]([C:32]1[CH:33]=[N:34][C:35]2[C:40]([CH:41]=1)=[CH:39][C:38]([O:42][CH:43]([S:47][CH3:48])[C:44](O)=[O:45])=[CH:37][CH:36]=2)#[CH:31]>CN(C)C=O.[Cl-].[Na+].O.C(N(CC)CC)C>[C:3]([C:2]([NH:1][C:44](=[O:45])[CH:43]([O:42][C:38]1[CH:39]=[C:40]2[C:35](=[CH:36][CH:37]=1)[N:34]=[CH:33][C:32]([C:30]#[CH:31])=[CH:41]2)[S:47][CH3:48])([CH3:7])[CH2:5][F:6])#[N:4]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 11007831HCID 11007831, compoundHCID 59565474(3-Ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid

Product 1

HCID 59565266HCID 59565266, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-amino-3-fluoro-2-methylpropionitrile (168 mg) in dry dimethylformamide (12 mL) were added triethylamine (0.22 mL), 1-hydroxy-7-azabenzotriazole (224 mg), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide.HCl (316 mg), then (3-ethynyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (450 mg). The reaction mixture was stirred at room temperature for 2 hours. The mixture was poured over brine and extracted twice with ethyl acetate (thrice). The organic layer was washed with water then with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude was purified by chromatography eluting with cyclohexane/ethyl acetate (3:2 by volume), to give N-(1-cyano-2-fluoro-1-methyl-ethyl)-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (483 mg) as an oil.

Workup

  1. extractionextracted twice with ethyl acetate (thrice)
  2. washThe organic layer was washed with water
  3. dry with materialwith brine, dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by chromatography
  7. washeluting with cyclohexane/ethyl acetate (3:2 by volume)

Sources & evidence

ORD record
ord-23695e87146241778a5e1875e061b048
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

Loading…