Triethylamine → [2-(4-Amino-phenyl)-ethyl]-[7-(3-chloro-propoxy)-quinazolin-4-yl]-amine

HRID 1468987Notes

Reaction equation

HRID 1468987 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH2:26])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(O)C>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][NH:26][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])=[CH:9][CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 728952-(4-Aminophenyl)ethylamineHCID 162215144-Chloro-7-(3-chloropropoxy)quinazoline

Product 1

HCID 67218600[2-(4-Amino-phenyl)-ethyl]-[7-(3-chloro-propoxy)-quinazolin-4-yl]-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloro-7-(3-chloro-propoxy)-quinazoline (synthesized as reported in J. Med. Chem. 2007, 50, 2213-2224) (100 mg, 0.389 mmol), 2-(4-aminophenyl)ethyl amine (63.6 mg, 0.467 mmol) and triethylamine (118.1 mg, 1.167 mmol) in ethanol (3 mL) was heated at 120° C. for 3 hours. The solution was cooled and the solid formed was filtered, washed with ethanol and then with dichloromethane to give the title compound as light yellow solid product (34 mg, 25%). 1H-NMR (300 MHz, CD3OD): 7.93-8.37 (s, 1H), 7.96 (d, J=9.0 Hz, 1H), 7.07-7.13 (m, 2H), 7.00-7.03 (d, J=8.1 Hz, 2H), 6.66-6.69 (d, J=8.4 Hz, 2H), 4.24-4.28 (t, 2H), 3.71-3.81 (m, 4H), 2.84-2.89 (t, 2H), 2.27-2.31 (m, 2H). LC-MS (ESI) m/z 357.3 (M+1).

Workup

  1. temperatureThe solution was cooled
  2. customthe solid formed
  3. filtrationwas filtered
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-09b0c579676a47bfb91cab35c6b837f4
Source dataset
uspto-grants-2015_04
Patent number
US09006252B2

Reaction notes

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