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Triethylamine → Tert-butyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-4-ylcarbamate

HRID 2062294
Notes
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Reaction equation

HRID 2062294 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=2[OH:20])[N:3]=1.C(N(CC)CC)C.[NH:28]1[CH2:33][CH2:32][CH:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:30][CH2:29]1>C(Cl)Cl>[F:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:20])[C:13]=1[C:4]1[N:3]=[C:2]([N:28]2[CH2:29][CH2:30][CH:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40])[CH2:32][CH2:33]2)[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 1361213752-(4-Chloro-7-methylquinazolin-2-yl)-3-fluorophenol

Product 1

HCID 136121470Tert-butyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-4-ylcarbamateYield 96%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 2-(4-chloro-7-methylquinazolin-2-yl)-3-fluorophenol (700 mg, 2.42 mmol) in 10 ml CH2Cl2 at 0° C. was added triethylamine (0.67 mL, 4.8 mmol) followed by the addition of tert-butyl piperidin-4-ylcarbamate (630 mg, 3.14 mmol) under an N2 atmosphere. The reaction was gradually warmed to room temperature and stirred overnight. The reaction mixture was then quenched with water, and the layers were separated. The aqueous layer was extracted twice with CH2Cl2, and the combined organic layers were dried over MgSO4, filtered, and concentrated to obtain tert-butyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-4-ylcarbamate (1.05 g, 96%) LC/MS: m/z 453.3 (M+H)+ at 2.60 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Workup

  1. customThe reaction mixture was then quenched with water
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted twice with CH2Cl2
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-67702b00a71f4766810b9c3fef5b996d
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08283354B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes