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Diisopropylethylamine → Methyl 4-((2-chloro-5-phenylquinazolin-4-ylamino)methyl)benzoate

HRID 2036785
Notes
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Reaction equation

HRID 2036785 reaction equation
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.C(N(C(C)C)CC)(C)C.[NH2:28][CH2:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[C:10]([NH:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:38][CH:39]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 571728Methyl 4-(aminomethyl)benzoateHCID 71741791HCID 71741791, compound

Product 1

HCID 86670615Methyl 4-((2-chloro-5-phenylquinazolin-4-ylamino)methyl)benzoateYield 37.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a solution of 2,4-dichloro-5-phenylquinazoline (1 g, 4 mmol) in THF (15 mL) was added diisopropylethyl amine (1.86 mL, 10.9 mmol) followed by methyl 4-(aminomethyl)benzoate (1.19 g, 7.21 mmol). Upon completion of addition, the reaction mixture was stirred for 12 h. At the conclusion of this period, the reaction mixture was diluted with ethyl acetate and then washed successively with water and brine. The combined organic layers were dried over Na2SO4, filtered and concentrated to yield a residue. The residue was purified by flash column chromatography using 6% ethyl acetate in petroleum ether to afford methyl 4-((2-chloro-5-phenylquinazolin-4-ylamino)methyl)benzoate (600 mg) as a white solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.92 (d, J=8.0 Hz, 2H), 7.80 (d, J=8.4 Hz, 1H), 7.70 (t, J=8.0 Hz, 1H), 7.38-7.33 (m, 5H), 7.22 (d, J=7.2 Hz, 1H), 7.02 (d, J=8.0 Hz, 2H), 5.56 (bs, 1H), 4.53 (d, J=4.8 Hz, 2H), 3.39 (s, 3H). LCMS Method O: retention time 2.12 min, [M+1]=404.0. HPLC Method B: purity 97.8%, retention time 18.17 min.

Workup

  1. additionUpon completion of addition
  2. washwashed successively with water and brine
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a residue
  7. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-b01581cffcdd44ddbe2c678fb2d07965
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575184B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes