N-Methylbenzylamine → N-Benzyl-6-chloro-N-methyl-2-{4-[2-(4-morpholinyl)ethoxy]phenyl}-1H-imidazo[4,5-b]pyridin-7-amine

HRID 2218395Notes

Reaction equation

HRID 2218395 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[C:4]2[N: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)[NH:8][C:5]2=[N:6][CH:7]=1.[CH3:27][NH:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(OCC)C>[CH2:29]([N:28]([CH3:27])[C:3]1[C:2]([Cl:1])=[CH:7][N:6]=[C:5]2[N:8]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[CH:15][CH:16]=3)[NH:10][C:4]=12)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 178478272HCID 178478272, compound

Product 1

HCID 10412763N-Benzyl-6-chloro-N-methyl-2-{4-[2-(4-morpholinyl)ethoxy]phenyl}-1H-imidazo[4,5-b]pyridin-7-amineYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6,7-Dichloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-3H-imidazo[4,5-b]pyridine (Example 206) (0.10 g, 0.25 mmol) and N-methylbenzylamine (0.7 ml) were heated to 180° C. for 3 h. The reaction mixture was diluted with diethyl ether (15 ml) and extracted with 2M HCl (40 ml). The aqueous phase was basified with 10M NaOH and extracted with EtOAc. The organic phase was evaporated in vacuo and the oily residue became crystalline. The crystals were washed with tert-butyl methyl ether to afford the pure product (42%).

Workup

  1. extractionextracted with 2M HCl (40 ml)
  2. extractionextracted with EtOAc
  3. customThe organic phase was evaporated in vacuo
  4. washThe crystals were washed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-04ee04d0494947b8850c3f2258ccad10
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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