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Triethylamine → Tert-butyl ({2-isobutyl-4-(4-methylphenyl)-6-[(2-methyl-1,3-thiazol-4-yl)methoxy]quinolin-3-yl}methyl)carbamate

HRID 1986441
Notes
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Reaction equation

HRID 1986441 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:5]2[C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:40][C:41]1[N:42]=[C:43]([CH3:46])[S:44][CH:45]=1.C(N(CC)CC)C>CN(C)C=O.O>[CH2:12]([C:7]1[C:6]([CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[C:5]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([O:1][CH2:40][C:41]3[N:42]=[C:43]([CH3:46])[S:44][CH:45]=3)[CH:3]=2)[N:8]=1)[CH:13]([CH3:15])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 51050241HCID 51050241, compound

Product 1

HCID 86605632Tert-butyl ({2-isobutyl-4-(4-methylphenyl)-6-[(2-methyl-1,3-thiazol-4-yl)methoxy]quinolin-3-yl}methyl)carbamateYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl {[6-hydroxy-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (0.40 g, 0.95 mmol) in N,N-dimethylformamide (10 ml) were added potassium carbonate (0.28 g, 2.0 mmol), 4-(chloromethyl)-2-methyl-1,3-thiazole hydrochloride (0.37 g, 2.0 mmol) and triethylamine (0.31 ml, 2.2 mmol) and the mixture was stirred at room temperature for 6 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl ({2-isobutyl-4-(4-methylphenyl)-6-[(2-methyl-1,3-thiazol-4-yl)methoxy]quinolin-3-yl}methyl)carbamate (0.32 g, yield 63%) as pale-yellow crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a45f8315d47849719d23ccf5fb4147fd
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07547710B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes