Benzylamine → HCID 11653595, compound

HRID 2381006Notes

Reaction equation

HRID 2381006 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[CH2:22]([NH:29][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 117381122-chloro-N-(4-methoxyphenyl)-N-methylquinazolin-4-amine

Product 1

HCID 11653595HCID 11653595, compoundYield 13.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2-chloro-quinazolin-4-yl)-(4-methoxyphenyl)-methylamine (150 mg, 0.5 mmol), benzyl amine (110 uL, 1.0 mmol) and triethyl amine (100 uL) in 5 mL of THF in a seal tube was heated overnight at 80° C. After cooling to room temperature the reaction mixture was diluted with 25 mL of ethyl acetate, washed with saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated. The crude was purified by column chromatography (35% ethyl acetate/hexane) to give the title compound (25 mg, 0.067 mmol, 13%). 1H NMR (CDCl3): 7.24-7.46 (m, 7H), 7.10 (m, 2H), 6.84-6.92 (m, 3H), 6.68 (ddd, J=8.1. 6.9, 1.5, 1H), 4.78 (d, J=6.5, 2H), 3.83 (s, 3H), 3.46 (s, 3H).

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by column chromatography (35% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ecafd05d503449f1aa4bf71102c26f51
Source dataset
uspto-grants-2012_09
Patent number
US08258145B2

Reaction notes

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