N,N-Diethyl-p-phenylenediamine → HCID 10414350, compound

HRID 2218398Notes

Reaction equation

HRID 2218398 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.[CH2:27]([N:29]([CH2:37][CH3:38])[C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1)[CH3:28]>COC(C)(C)C>[Cl:1][C:2]1[C:3]([NH:36][C:33]2[CH:32]=[CH:31][C:30]([N:29]([CH2:37][CH3:38])[CH2:27][CH3:28])=[CH:35][CH:34]=2)=[C:4]2[NH:10][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)=[N:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 7120N,N-Diethyl-p-phenylenediamineHCID 178478272HCID 178478272, compound

Product 1

HCID 10414350HCID 10414350, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

6,7-Dichloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-3H-imidazo[4,5-b]pyridine (Example 206) (0.020 g, 0.051 mmol) and N,N-diethyl-1,4-phenylenediamine (0.1 g) were heated to 180° C. for 2 h. The reaction mixture was diluted with tert-butyl methyl ether (5 ml) and extracted with 2M HCl (20 ml). The aqueous phase was basified with 10M NaOH and extracted with EtOAc. The organic phase was evaporated in vacuo and the residue was dissolved in CH3CN (2 ml) and purified by HPLC-C18, giving the title product (56%).

Workup

  1. extractionextracted with 2M HCl (20 ml)
  2. extractionextracted with EtOAc
  3. customThe organic phase was evaporated in vacuo
  4. dissolutionthe residue was dissolved in CH3CN (2 ml)
  5. custompurified by HPLC-C18

Sources & evidence

ORD record
ord-e0c458abff4442a2a2cae48953f400ca
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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