Isopropylamine → HCID 49782712, compound

HRID 1923568Notes

Reaction equation

HRID 1923568 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.C[O:10][C:11]([C:13]1[S:17][C:16](/[CH:18]=[CH:19]/[C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])=[N:15][C:14]=1[CH3:32])=O>O1CCOCC1.C1(C)C=CC=CC=1>[CH:1]([NH:4][C:11]([C:13]1[S:17][C:16](/[CH:18]=[CH:19]/[C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])=[N:15][C:14]=1[CH3:32])=[O:10])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 66643663HCID 66643663, compound

Product 1

HCID 49782712HCID 49782712, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

To a stirred solution of isopropylamine (56 mg, 0.95 mmol) in dioxane (2 mL) under argon and at room temperature was added trimethylaluminium (0.47 mL of a 2M solution in toluene, 0.94 mmol). After 1 h, a solution of 4-methyl-2-[(E)-2-(5-methyl-3-phenyl-isoxazol-4-yl)-vinyl]-thiazole-5-carboxylic acid methyl ester (80 mg, 0.24 mmol) in dioxane (2 mL) was added and the reaction mixture warmed to 90° C. After 24 h, the reaction mixture was cooled, quenched with ice and Seignettes's salt solution, then extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, 10 to 80% ethyl acetate in heptane) gave the title compound (40 mg, 46%) as an off white solid. MS: m/e=368.1 [M+H]+.

Workup

  1. waitAfter 24 h
  2. temperaturethe reaction mixture was cooled
  3. customquenched with ice and Seignettes's salt solution
  4. extractionextracted with ethyl acetate
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica, 10 to 80% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-f7c2aa6e907f4ffdbc68ac77558983aa
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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