Triethylamine → N-{4-[(4-Methoxy-phenyl)-methyl-amino]-quinazolin-2-ylmethyl}-nicotinamide

HRID 1876221Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[N:12]=[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.Cl.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([N:13]([CH3:14])[C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=[C:3]([CH2:2][NH:1][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[N:27][CH:26]=3)[N:12]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To (2-aminomethyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methyl-amine (100 mg, 0.34 mmol) and nicotinoyl chloride hydrochloride (91 mg, 0.51 mmol) in CH2Cl2 (3 mL) at 0° C. was added triethylamine (167 mg, 1.2 mmol). The reaction was stirred for 2 h at 0° C. The mixture was washed successively with H2O, 0.1 M HCl, H2O and 5% NaHCO3. The reaction was extracted with EtOAc (3×10 mL), washed with brine, dried (MgSO4) and concentrated providing 64 mg of the title compound. 1H NMR (CDCl3) δ 8.76 (s, 1H), 8.29 (d, 1H), 8.11 (s, 1H), 7.78 (d, 1H), 7.58 (t, 1H), 7.45 (t, 1H), 7.14 (d, 2H), 7.05-7.01 (m, 2), 6.93 (d, 2H), 4.85 (s, 2H), 3.85 (s, 3H), 3.61 (s, 3H); LC-MS (ESI+; 400 ([M+H]+)).

Workup

washThe mixture was washed successively with H2O, 0.1 M HCl, H2O and 5% NaHCO3
extractionThe reaction was extracted with EtOAc (3×10 mL)
washwashed with brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-26818489e6a741aba216cc09bc06c239
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

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