Isopropylamine → HCID 49782487, compound

HRID 1923496Notes

Reaction equation

HRID 1923496 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.[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[S:24][C:25]([C:28](O)=[O:29])=[CH:26][N:27]=1>O1CCOCC1.C1(C)C=CC=CC=1>[CH:1]([NH:4][C:28]([C:25]1[S:24][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:27][CH:26]=1)=[O:29])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 66643786HCID 66643786, compound

Product 1

HCID 49782487HCID 49782487, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

To a stirred solution of isopropylamine (75 mg, 1.27 mmol) in dioxane (5 mL) under argon and at room temperature was added trimethylaluminium (0.6 mL of a 2M solution in toluene, 1.2 ml). After 1 h, a solution of 2-[2-(5-methyl-3-phenyl-isoxazol-4-yl)-ethyl]-thiazole-5-carboxylic acid (100 mg, 0.32 mmol) in dioxane (5 mL) was added and the reaction mixture warmed to 90° C. After 3 h, the reaction mixture was cooled, quenched with ice water and extracted with dichloromethane. The combined extracts were washed with Seignette's salt solution then dried, filtered, and concentrated. Purification by chromatography (silica, 0 to 3% methanol in dichloromethane) gave the title compound (78 mg, 69%) as a pale yellow oil. MS: m/e=356.1 [M+H]+.

Workup

  1. waitAfter 3 h
  2. temperaturethe reaction mixture was cooled
  3. customquenched with ice water
  4. extractionextracted with dichloromethane
  5. washThe combined extracts were washed with Seignette's salt solution
  6. customthen dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by chromatography (silica, 0 to 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9ae37eb9b87b46fd8b4d1800aeef15dd
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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