4-Pyrrolidinopyridine → HCID 11496521, compound

HRID 905613Notes

Reaction equation

HRID 905613 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:28])[N:6]2[CH2:16][CH2:17][O:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=[O:22].[CH3:29][N:30]([CH3:35])[CH2:31][CH2:32][CH2:33]O.N1(C2C=CN=CC=2)CCCC1>ClCCl>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:28])[N:6]2[CH2:16][CH2:17][O:18][C:19]1[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([O:23][CH2:33][CH2:32][CH2:31][N:30]([CH3:35])[CH3:29])=[O:22]

Participants

5

Reactant 3

HCID 755674-PyrrolidinopyridineHCID 766463-(Dimethylamino)-1-propanolHCID 58942868HCID 58942868, compound

Product 1

HCID 11496521HCID 11496521, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound obtained in Example 2-9 step (iii) (50 mg) was dissolved in dichloromethane (5 ml), and thereto were added 3-(dimethylamino)propane-1-ol (0.016 ml), 4-pyrrolidin-1-ylpyridine (2 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbondiimide iodine methyl (42 mg). The mixture was stirred at room temperature for 96 hours and applied to a cartridge of SCX resin. The resin was washed with acetonitrile and the fractions were collected by application of 10% aqueous ammonium solution-acetonitrile, and purified by RPHPLC to give the titled compound.

Workup

  1. washThe resin was washed with acetonitrile
  2. customthe fractions were collected by application of 10% aqueous ammonium solution-acetonitrile
  3. custompurified by RPHPLC

Sources & evidence

ORD record
ord-4275bebd334746e1855b822ea3a78065
Source dataset
uspto-grants-2011_09
Patent number
US08012964B2

Reaction notes

Loading…