3-Aminopyrrolidine → HCID 11744098, compound

HRID 2218388Notes

Reaction equation

HRID 2218388 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.[NH2:27][CH:28]1[CH2:32][CH2:31][NH:30][CH2:29]1>CCOC(C)=O>[Cl:1][C:2]1[C:3]([N:30]2[CH2:31][CH2:32][CH:28]([NH2:27])[CH2:29]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 1644013-AminopyrrolidineHCID 178478272HCID 178478272, compound

Product 1

HCID 11744098HCID 11744098, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

6,7-Dichloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-3H-imidazo[4,5-b]pyridine (Example 206) (40 mg, 110 μmol) and 3-aminopyrrolidine (0.5 ml) were heated at 195° C. for 15 min and then allowed to cool. The reaction mixture was diluted with EtOAc (5 ml) and extracted with 4M HCl (4 ml). The aqueous phase was neutralized with saturated aqueous NaHCO3 and extracted with EtOAc (4 ml). The organic phase was evaporated in vacuo and the residue dissolved in acetonitrile (2 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 (30 mg, 61%).

Workup

  1. temperatureto cool
  2. extractionextracted with 4M HCl (4 ml)
  3. extractionextracted with EtOAc (4 ml)
  4. customThe organic phase was evaporated in vacuo
  5. dissolutionthe residue dissolved in acetonitrile (2 ml)
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in EtOAc (5 ml)
  8. washThis solution was washed with saturated aqueous NaHCO3 (5 ml) and brine (2 ml)
  9. dry with materialThe organic phase was dried (MgSO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-8aa787116204475b8d0819431eb00833
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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