HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Isopropylamine → 2-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid iso-propylamide

HRID 1923543
Notes
Print preview

Reaction equation

HRID 1923543 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].C[Al](C)C.[CH2:9]([C:13]1[C:17]([CH2:18][CH2:19][C:20]2[S:21][C:22]([C:26](O)=[O:27])=[C:23]([CH3:25])[N:24]=2)=[C:16]([CH3:29])[O:15][N:14]=1)[CH2:10][CH2:11][CH3:12]>O1CCOCC1.C1(C)C=CC=CC=1>[CH:1]([NH:4][C:26]([C:22]1[S:21][C:20]([CH2:19][CH2:18][C:17]2[C:13]([CH2:9][CH2:10][CH2:11][CH3:12])=[N:14][O:15][C:16]=2[CH3:29])=[N:24][C:23]=1[CH3:25])=[O:27])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 666436692-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid

Product 1

HCID 497820372-[2-(3-Butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid iso-propylamideYield 44.7%

Reagents, catalysts & solvents 2

HCID 1140
Toluene
Solvent
HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
90 °C

Procedure

To a stirred solution of isopropylamine (77 mg, 1.3 mmol) in dioxane (3 mL) under argon and at room temperature was added trimethylaluminium (0.65 mL of a 2M solution in toluene, 1.3 mmol). After 1 h, a solution of 2-[2-(3-butyl-5-methyl-isoxazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid (100 mg, 0.32 mmol) in dioxane (4 mL) was added and the reaction mixture heated at 90° C. overnight. The reaction mixture was then 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 5% methanol in dichloromethane) gave the title compound (50 mg, 44%) as a light yellow oil. MS: m/e=350.5 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-d44bd3e46c1b44eabe2876078a11c2f2
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178522B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes