Acetic Acid → N-(3-ethynylphenyl)-6-(2-(2-(2-(2-((4-((3-ethynylphenyl)-amino)-6-(2-methoxyethoxy)quinazolin-7-yl)-oxy)ethoxy)ethoxy)ethoxy)ethoxy)-7-(2-methoxyethoxy)quinazolin-4-amine

HRID 1405970Notes

Reaction equation

HRID 1405970 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26](/[N:28]=[CH:29]/[N:30](C)C)[C:25]([C:33]#[N:34])=[CH:24][C:23]=2[O:35][CH2:36][CH2:37][O:38][CH3:39])[C:6]([O:40][CH2:41][CH2:42][O:43][CH3:44])=[CH:5][C:4]=1/[N:45]=[CH:46]/[N:47](C)C)#[N:2].[C:50]([C:52]1[CH:53]=[C:54]([CH:56]=[CH:57][CH:58]=1)N)#[CH:51].[CH3:59][C:60](O)=O>CCOCC>[C:50]([C:52]1[CH:53]=[C:54]([NH:2][C:1]2[C:3]3[C:4](=[CH:5][C:6]([O:40][CH2:41][CH2:42][O:43][CH3:44])=[C:7]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][C:22]4[CH:27]=[C:26]5[C:25]([C:33]([NH:34][C:3]6[CH:8]=[CH:7][CH:6]=[C:5]([C:60]#[CH:59])[CH:4]=6)=[N:30][CH:29]=[N:28]5)=[CH:24][C:23]=4[O:35][CH2:36][CH2:37][O:38][CH3:39])[CH:8]=3)[N:45]=[CH:46][N:47]=2)[CH:56]=[CH:57][CH:58]=1)#[CH:51]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 104682Benzenamine, 3-ethynyl-HCID 178496147HCID 178496147, compound

Product 1

HCID 71813202N-(3-ethynylphenyl)-6-(2-(2-(2-(2-((4-((3-ethynylphenyl)-amino)-6-(2-methoxyethoxy)quinazolin-7-yl)-oxy)ethoxy)ethoxy)ethoxy)ethoxy)-7-(2-methoxyethoxy)quinazolin-4-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(E)-N′-(2-cyano-4-(2-(2-(2-(2-(4-cyano-5-((E)-((dimethylamino)methylene)amino)-2-(2-methoxyethoxy)phenoxy)ethoxy)ethoxy)ethoxy)ethoxy)-5-(2-methoxyethoxy)phenyl)-N,N-dimethylformimidamide (0.2 g), 3-ethynylaniline (0.11 g) were added to AcOH (5 mL), the resulting mixture was heated at reflux for 3 h under N2 atmospheres. After reaction finished, the mixture was diluted with Et2O (30 ml) and solid was collected. The solid was washed with Et2O and air-dried to give N-(3-ethynylphenyl)-6-(2-(2-(2-(2-((4-((3-ethynylphenyl)-amino)-6-(2-methoxyethoxy)quinazolin-7-yl)-oxy)ethoxy)ethoxy)ethoxy)ethoxy)-7-(2-methoxyethoxy)quinazolin-4-amine (0.14 g, dimer 3) as a brown solid. 1H-NMR (400 MHz, DMSO-d6): δ: 9.46 (br, 2H), 8.48 (s, 2H), 7.98 (s, 2H), 7.89-7.83 (m, 4H), 7.40-7.37 (m, 2H), 7.22-7.19 (m, 4H), 4.33-4.25 (m, 8H), 4.21 (s, 1H), 4.20 (s, 1H), 3.90-3.80 (m, 4H), 3.80-3.70 (m, 4H), 370-7.60 (m, 4H), 3.60-3.50 (m, 4H), 3.35 (s, 3H), 3.34 (s, 3H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 3 h under N2 atmospheres
  3. customAfter reaction
  4. customwas collected
  5. washThe solid was washed with Et2O
  6. customair-dried

Sources & evidence

ORD record
ord-b88cf1c5a8da401fa74e9e1d49b487bc
Source dataset
uspto-grants-2014_12
Patent number
US08916572B2

Reaction notes

Loading…