Methanol → HCID 22667110, compound

HRID 1008392Notes

Reaction equation

HRID 1008392 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.[CH2:35]([NH2:40])[CH2:36][CH2:37][CH2:38][CH3:39].CO>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:27]([NH:40][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:33])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8060PentylamineHCID 94429TriphosgeneHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)aniline

Product 1

HCID 22667110HCID 22667110, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.2 ml), and a solutioin of triphosgene (50 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, amylamine (26 μl) was added to the reaction solution, and the mixture was stirred at room temperature overnight. Methanol was added to the reaction solution, and the mixture was purified by HPLC by development with chloroform/methanol to give 21 mg (yield 30%) of the title compound. 1H-NMR (DMSO-d6, 400 MHz): δ 0.89 (t, J=7.1 Hz, 3H), 1.27-1.47 (m, 4H), 1.41-1.48 (m, 2H), 3.06-3.11 (m, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 6.13 (t, J=5.6 Hz, 1H), 7.15 (d, J=9.0 Hz, 2H), 7.37 (s, 1H), 7.46 (d, J=8.8 Hz, 2H), 7.55 (s, 1H), 8.47 (br, 1H), 8.53 (s, 1H).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customthe mixture was purified by HPLC by development with chloroform/methanol

Sources & evidence

ORD record
ord-521cfd34076546de942769cde7b258ef
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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