Hydrochloric Acid → HCID 59565295, compound

HRID 1962855Notes

Reaction equation

HRID 1962855 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.[I:30][C:31]1[CH:32]=[N:33][C:34]2[C:39]([CH:40]=1)=[CH:38][C:37]([O:41][CH:42]([S:46][CH3:47])[C:43](O)=[O:44])=[CH:36][C:35]=2[CH3:48]>CN(C)C=O.[Cl-].[Na+].O.C(N(CC)CC)C>[C:3]([C:2]([NH:1][C:43](=[O:44])[CH:42]([O:41][C:37]1[CH:38]=[C:39]2[C:34](=[C:35]([CH3:48])[CH:36]=1)[N:33]=[CH:32][C:31]([I:30])=[CH:40]2)[S:46][CH3:47])([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 67213779HCID 67213779, compound

Product 1

HCID 59565295HCID 59565295, compoundYield 62.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-amino-3-fluoro-2-methylpropionitrile (315 mg) in dry dimethylformamide (20 mL) were added triethylamine (0.43 mL), 1-hydroxy-7-azabenzotriazole (420 mg), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide.HCl (591 mg), then (3-iodo-8-methyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (1.2 g). The reaction mixture was stirred at room temperature for 18 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-iodo-8-methyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (906 mg) as a solid.

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-1317005b3aff43b4988ee74f24e33cb9
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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