2,5-Dimethoxytetrahydrofuran → HCID 69210850, compound

HRID 2218387Notes

Reaction equation

HRID 2218387 reaction equation
[Cl:1][C:2]1[C:3]([NH2:26])=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:13][CH:12]=3)=[N:8][C:5]2=[N:6][CH:7]=1.CO[CH:29]1[CH2:33][CH2:32][CH:31](OC)O1>C(O)(=O)C>[Cl:1][C:2]1[C:3]([N:26]2[CH:29]=[CH:33][CH:32]=[CH:31]2)=[C:4]2[NH:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[CH:13][CH:12]=3)=[N:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 9976645HCID 9976645, compound

Product 1

HCID 69210850HCID 69210850, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

6-Chloro-2-{4-[2-(4-morpholinyl)ethoxy]phenyl}-1H-imidazo[4,5-b]pyridin-7-amine (Example 212) (17 mg, 45 μmol) was dissolved in acetic acid (5 ml). 2,5-Dimethoxytetrahydrofuran (0.20 ml) was added and the mixture heated (110° C., 3 h) and then allowed to cool and the solvents and excess reagents were removed in vacuo. The residual brown oil was dissolved in acetonitrile (1 ml) and subjected to semi-preparative HPLC-C18. The appropriate fractions were pooled and evaporated in vacuo. The residue was dissolved in EtOAc (5 ml). This solution was washed with saturated aqueous NaHCO3 (5 ml) and brine (2 ml). The organic phase was dried (MgSO4) and evaporated in vacuo to afford the pure product (17 mg, 88%) as a beige powder.

Workup

  1. temperatureto cool
  2. customthe solvents and excess reagents were removed in vacuo
  3. dissolutionThe residual brown oil was dissolved in acetonitrile (1 ml)
  4. customevaporated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc (5 ml)
  6. washThis solution was washed with saturated aqueous NaHCO3 (5 ml) and brine (2 ml)
  7. dry with materialThe organic phase was dried (MgSO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-5a23e9ed14e541a3afcbfb9e1bdce88f
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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