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

Ethyl Acetate → N,N-Dicyclopropylmethyl-N-[7-[2-methoxy-6-methyl-4-(1,3-thiazol-2-yl)phenyl]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine

HRID 9218
Notes
Print preview

Reaction equation

HRID 9218 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:14]3[N:15]=[C:16]([S:27][CH3:28])[C:17]([N:18]([CH2:23][CH:24]4[CH2:26][CH2:25]4)[CH2:19][CH:20]4[CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11][CH:10]=2)=[C:4]([O:29][CH3:30])[CH:3]=1.C([Sn]([C:44]1[S:45][CH:46]=[CH:47][N:48]=1)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:20]1([CH2:19][N:18]([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C:17]2[C:16]([S:27][CH3:28])=[N:15][N:14]3[C:9]([C:5]4[C:6]([CH3:8])=[CH:7][C:2]([C:44]5[S:45][CH:46]=[CH:47][N:48]=5)=[CH:3][C:4]=4[O:29][CH3:30])=[CH:10][CH:11]=[CH:12][C:13]=23)[CH2:22][CH2:21]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 21984504N-[7-(4-bromo-2-methoxy-6-methylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine

Product 1

HCID 21984786N,N-Dicyclopropylmethyl-N-[7-[2-methoxy-6-methyl-4-(1,3-thiazol-2-yl)phenyl]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amineYield 66.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

After dissolving N-[7-(4-bromo-2-methoxy-6-methylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine (45 mg) in toluene (0.60 mL), tributylstannylthiazole (52 mg) and tetrakis (triphenylphosphine)palladium (0) complex (9 mg) were added, the mixture was heated and stirred at 120° C. for 2 hours and then cooled to room temperature, and ethyl acetate was added. After filtering out the precipitated insoluble portion, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5) to obtain the title compound (30 mg) as white crystals.

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperaturecooled to room temperature
  4. filtrationAfter filtering out the precipitated insoluble portion
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5)

Sources & evidence

ORD record
ord-1d28720315fc4f67a65cac0df851c4fc
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091215B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes