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2-[(Thiophen-2-ylmethyl)-amino]-ethanol → 4-[(2-Hydroxy-ethyl)-thiophen-2-ylmethyl-amino]-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester

HRID 1831666
Notes
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Reaction equation

HRID 1831666 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9](Cl)=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21].[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH2:28][NH:29][CH2:30][CH2:31][OH:32]>CN1CCCC1=O>[CH3:1][O:2][C:3](=[O:22])[C:4]1[C:9]([N:29]([CH2:30][CH2:31][OH:32])[CH2:28][C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:7]([CH3:11])=[N:6][C:5]=1[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 31544482-[(Thiophen-2-ylmethyl)-amino]-ethanolHCID 248056514-Chloro-2-(2,4,6-trimethyl-phenoxy)-6-methyl-nicotinic acid methyl ester

Product 1

HCID 695878334-[(2-Hydroxy-ethyl)-thiophen-2-ylmethyl-amino]-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-chloro-6-methyl-2-(2,4,6-trimethyl-phenoxy)-nicotinic acid methyl ester and 2-[(thiophen-2-ylmethyl)-amino]-ethanol in 1-methyl-2-pyrrolidinone was heated at 130° C. overnight. The mixture was quenched with water, brine and extracted with ethyl acetate. The organic layer was dried and concentrated to dryness. The residue was purified through silica gel column chromatography to give the title compound. 1H NMR (CDCl3) d 7.22(m,1H), 6.94m,2H), 6.84(s,2H), 6.44(s,1H), 4.52(s,2H), 3.91(s,3H), 3.679t,2H), 3.369t,2H), 2.279s,3H), 2.20(s,3H), 2.07(s,6H) ppm.

Workup

  1. customThe mixture was quenched with water, brine
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated to dryness
  5. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-46e202f476644b269efde3d8be5af1fe
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07067664B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes