2,5-Dimethoxytetrahydrofuran → HCID 10131501, compound

HRID 586329Notes

Reaction equation

HRID 586329 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[N:7][N:6]2[C:9]([C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)=[CH:10][N:11]=[C:5]2[N:4]=1.CO[CH:23]1[CH2:27][CH2:26][CH:25](OC)O1>C(O)(=O)C>[N:18]1([C:14]2[CH:13]=[C:12]([C:9]3[N:6]4[N:7]=[CH:8][C:3]([C:2]([F:1])([F:19])[F:20])=[N:4][C:5]4=[N:11][CH:10]=3)[CH:17]=[CH:16][CH:15]=2)[CH:23]=[CH:27][CH:26]=[CH:25]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 22329549HCID 22329549, compound

Product 1

HCID 10131501HCID 10131501, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-(3-trifluoromethylimidazo[1,2-b][1,2,4]triazin-7-yl)phenylamine and 2,5-dimethoxytetrahydrofuran in acetic acid was heated at 130° C. for 20 min. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 10% Et2O/isohexane) to give 40 mg (62%) of the title compound: 1H NMR (400 MHz, CDCl3) δ 6.41 (2H, t, J 2.2 Hz), 7.18 (2H, t, J 2.2 Hz), 7.51 (1H, ddd, J 8.3, 2.5, 1.1 Hz), 7.62 (1H, t, J 8.3 Hz), 7.92 (1H, dt, J 8.8, 1.1 Hz), 8.21 (1H, t, J 2.2 Hz), 8.66 (1H, s), 8.81 (1H, s); MS (ES+) m/z 330 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (silica gel, 10% Et2O/isohexane)

Sources & evidence

ORD record
ord-7c44cfa46bc84ef5a3969d32c76c76c0
Source dataset
uspto-grants-2005_08
Patent number
US06936608B2

Reaction notes

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