Morpholine → HCID 178492970, compound

HRID 2218425Notes

Reaction equation

HRID 2218425 reaction equation
[Cl:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19]Cl)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Cl:1][C:2]1[C:3]([O:21][CH3:22])=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 178492968HCID 178492968, compound

Product 1

HCID 178492970HCID 178492970, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

6-Chloro-2-[4-(2-chloroethoxy)phenyl]-7-methoxy-3H-imidazo[4,5-b]pyridine (0.27 g, 0.8 mmol), morpholine (0.22 ml, 2.52 mmol) and Hünig's base (1.42 ml, 8.15 mmol) were dissolved in NMP (20 ml) and the mixture was heated at 100° C. for 9 h. The NMP was partly removed by evaporation, after which water was added. The precipitated crude material was purified by column chromatography (dichloromethane/methanol 95:5), giving the title product (0.022 g, 7%).

Workup

  1. customThe NMP was partly removed by evaporation
  2. additionafter which water was added
  3. customThe precipitated crude material
  4. customwas purified by column chromatography (dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-af042218696b4caf9d9fa87391dc1833
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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