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

Ethanolamine → HCID 66571223, compound

HRID 81995
Notes
Print preview

Reaction equation

HRID 81995 reaction equation
Cl[C:2]1[N:3]([CH2:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:4]2[C:13]3[CH:12]=[C:11]([O:14][CH3:15])[C:10]([C:16]4[C:17]([CH3:22])=[N:18][O:19][C:20]=4[CH3:21])=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:23]=1.[CH2:31]([CH2:33][NH2:34])[OH:32]>CN1C(=O)CCC1.CS(C)=O>[CH3:22][C:17]1[C:16]([C:10]2[C:11]([O:14][CH3:15])=[CH:12][C:13]3[C:4]4[N:3]([CH2:24][CH:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)[C:2]([NH:34][CH2:33][CH2:31][OH:32])=[N:23][C:5]=4[CH:6]=[N:7][C:8]=3[CH:9]=2)=[C:20]([CH3:21])[O:19][N:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 700EthanolamineHCID 709814012-chloro-7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 66571223HCID 66571223, compoundYield 5.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 13387N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
180 °C

Procedure

2-Chloro-7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline (for a preparation see Intermediate 15) (14 mg, 0.033 mmol) and ethanolamine (0.020 ml, 0.327 mmol) were dissolved in NMP (2 ml) and heated at 180° C. in the microwave for 1 h, then cooled and loaded onto a 10 g SCX-2 cartridge, washing with methanol (30 ml). The cartridge was then eluted with 2M methanolic ammonia (30 ml) and the eluant evaporated in vacuo to give a sparingly soluble brown gum. This was dissolved in DMSO (1 ml) and purified by MDAP (formate) to give 2-{[7-(3,5-dimethyl-4-isoxazolyl)-8-(methyloxy)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-yl]amino}ethanol (0.80 mg, 1.772 μmol, 5.40% yield) as a pale yellow glass. LCMS (formate) Rt 0.62 min, MH+ 452

Workup

  1. temperaturecooled
  2. washwashing with methanol (30 ml)
  3. washThe cartridge was then eluted with 2M methanolic ammonia (30 ml)
  4. customthe eluant evaporated in vacuo
  5. customto give a sparingly soluble brown gum
  6. custompurified by MDAP (formate)

Sources & evidence

ORD record
ord-7ad33877c830495db2fd0b876ada88f8
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846709B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes