Diisopropylethylamine → HCID 86702330, compound

HRID 2279074Notes

Reaction equation

HRID 2279074 reaction equation
C(N(C(C)C)CC)(C)C.Cl[C:11]1[N:16]=[C:15]([NH:17][C:18]2[C:19]([O:24][CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=2)[C:14]([N+:26]([O-:28])=[O:27])=[CH:13][CH:12]=1.Cl.[F:30][C:31]1[CH:32]=[CH:33][C:34]([C@@H:37]([NH2:39])[CH3:38])=[N:35][CH:36]=1>C(O)CCC.C(OCC)(=O)C>[F:30][C:31]1[CH:32]=[CH:33][C:34]([C@@H:37]([NH:39][C:11]2[N:16]=[C:15]([NH:17][C:18]3[C:19]([O:24][CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=3)[C:14]([N+:26]([O-:28])=[O:27])=[CH:13][CH:12]=2)[CH3:38])=[N:35][CH:36]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 67123789(S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochlorideHCID 86702329HCID 86702329, compound

Product 1

HCID 86702330HCID 86702330, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Diisopropylethylamine (0.49 mL, 2.81 mmol) was added to a solution of 6-chloro-N-(2-methoxypyridin-3-yl)-3-nitropyridin-2-amine (Preparation 22a, 0.26 g, 0.69 mmol) and (S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride (prepared according to the method described in WO2006/82392A1, 0.13 g, 0.74 mmol) in butanol (5 mL) and the resulting mixture was stirred at 80° C. overnight. Subsequently, the reaction was cooled down, diluted with ethyl acetate and washed with brine (×3). The organic phase was separated, dried over anhydrous magnesium sulphate and the solvent removed under reduced pressure. The residue was purified by flash chromatography (hexanes 100% to 1:1 hexanes/ethyl acetate) to give the title compound (253 mg, 94%) as a yellow solid.

Workup

  1. customprepared
  2. temperatureSubsequently, the reaction was cooled down
  3. washwashed with brine (×3)
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by flash chromatography (hexanes 100% to 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-66bf45ea039e467886c2c6923da260a9
Source dataset
uspto-grants-2015_09
Patent number
US09133200B2

Reaction notes

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