Isopropylamine → HCID 46872635, compound

HRID 1942286Notes

Reaction equation

HRID 1942286 reaction equation
C[Al](C)C.[CH:5]([NH2:8])([CH3:7])[CH3:6].[CH3:9][C:10]1[O:14][N:13]=[C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:11]=1[CH2:21][CH2:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][N:24]=1>O1CCOCC1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>[CH:5]([NH:8][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][C:23]([CH2:22][CH2:21][C:11]2[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][O:14][C:10]=2[CH3:9])=[N:24][CH:25]=1)([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 66618938HCID 66618938, compound

Product 1

HCID 46872635HCID 46872635, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 9357Potassium Sodium TartrateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

A solution of trimethyl aluminium (2 M in toluene, 0.32 mL, 0.65 mmol) was added dropwise to a solution of isopropylamine (38 mg, 0.65 mmol) in dioxane (1.5 mL) under argon and at room temperature. After 1 h a solution of 6-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-nicotinic acid (50 mg, 0.16 mmol) in dioxane (1.5 mL) was added and the reaction mixture warmed to 90° C. After 15 h, the reaction mixture was cooled and carefully diluted with Seignette salt solution (0.5 mL). The mixture was filtered, the filter cake washed with dichloromethane, then the combined filtrates were concentrated. Purification by chromatography (silica, dichloromethane:methanol 100:0 to 96:4) afforded the title compound (45 mg, 79%) as a light yellow oil. MS: m/e=350.5 [M+H]+.

Workup

  1. temperaturethe reaction mixture was cooled
  2. filtrationThe mixture was filtered
  3. washthe filter cake washed with dichloromethane
  4. concentrationthe combined filtrates were concentrated
  5. customPurification by chromatography (silica, dichloromethane:methanol 100:0 to 96:4)

Sources & evidence

ORD record
ord-10dd87a2d6584777bef8174464676246
Source dataset
uspto-grants-2013_03
Patent number
US08389550B2

Reaction notes

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