Sodium Chloride → (2R)-2-(5-cyano-3-fluoro-6-(quinolin-6-ylamino)pyridin-2-ylamino)-4-methylpentanamide

HRID 340511Notes

Reaction equation

HRID 340511 reaction equation
C(=O)([O-])[O-].[Ca+2].[NH2:6][C@@H:7]([C:12]([NH2:14])=[O:13])[CH2:8][CH:9]([CH3:11])[CH3:10].Cl.Cl[C:17]1[C:24]([F:25])=[CH:23][C:20]([C:21]#[N:22])=[C:19]([NH:26][C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[N:33]=[CH:32][CH:31]=[CH:30]3)[N:18]=1.[Cl-].[Na+]>C(OCC)(=O)C.O.O1CCOCC1>[C:21]([C:20]1[CH:23]=[C:24]([F:25])[C:17]([NH:6][C@H:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C:12]([NH2:14])=[O:13])=[N:18][C:19]=1[NH:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[N:33]=[CH:32][CH:31]=[CH:30]2)#[N:22]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10112Calcium CarbonateHCID 56776963(R)-2-Amino-4-methylpentanamide hydrochlorideHCID 866838496-Chloro-5-fluoro-2-(quinolin-6-ylamino)nicotinonitrile

Product 1

HCID 86683890(2R)-2-(5-cyano-3-fluoro-6-(quinolin-6-ylamino)pyridin-2-ylamino)-4-methylpentanamideYield 83.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Calcium carbonate (138 mg) and D-leucinamide•hydrochloride (83 mg) were added to a 1,4-dioxane (1 ml) solution containing 6-chloro-5-fluoro-2-(quinolin-6-ylamino)nicotinonitrile (30 mg), followed by reflux for 15 hours. The reaction mixture was cooled to room temperature, and water, sodium chloride, and ethyl acetate were added. The organic layer was collected and dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. Diisopropylether was added to the obtained residue, solid matter was collected by filtration, and a yellow solid of (2R)-2-(5-cyano-3-fluoro-6-(quinolin-6-ylamino)pyridin-2-ylamino)-4-methylpentanamide (33 mg) was thus obtained.

Workup

  1. temperatureby reflux for 15 hours
  2. customThe organic layer was collected
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. additionDiisopropylether was added to the obtained residue, solid matter
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-a7c2878e92e24f2786150a1652b03fb6
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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