1,3-Propanediamine, N1,N1,N3-trimethyl- → 3-{8-(2,6-difluorophenyl)-2-[[3-(dimethylamino)propyl](methyl)amino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl}-4-methyl-N-propylbenzamide

HRID 2245090Notes

Reaction equation

HRID 2245090 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16](S(C)(=O)=O)[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:28]=[CH:29][C:30]=3[CH3:31])[C:22]([NH:24][CH2:25][CH2:26][CH3:27])=[O:23])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:36].[CH3:37][N:38]([CH3:44])[CH2:39][CH2:40][CH2:41][NH:42][CH3:43]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[C:14]2[N:15]=[C:16]([N:42]([CH2:41][CH2:40][CH2:39][N:38]([CH3:44])[CH3:37])[CH3:43])[N:17]=[C:18]([C:19]3[CH:20]=[C:21]([CH:28]=[CH:29][C:30]=3[CH3:31])[C:22]([NH:24][CH2:25][CH2:26][CH3:27])=[O:23])[C:13]=2[CH:12]=[CH:11][C:10]1=[O:36]

Participants

4

Reactant 2

HCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 592126843-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide

Product 1

HCID 592127153-{8-(2,6-difluorophenyl)-2-[[3-(dimethylamino)propyl](methyl)amino]-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl}-4-methyl-N-propylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[8-(2,6-difluorophenyl)-2-(methylsulfonyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-propylbenzamide (0.04 g, 0.078 mmol), N,N,N′-trimethyl-1,3-propanediamine (0.134 g, 0.115 mmol), and TEA (0.016 g, 0.156 mmol) were combined in CH2Cl2 (5 mL) and stirred under argon at room temperature. The solvents were pumped off in vacuo. The residue was flash chromatographed on silica gel (10 g) eluted with CH2Cl2 to 6:1:0.1, CH2Cl2:ethanol:NH4OH. The compound had an impurity which was removed by filtering through a silica gel plug with 3% MeOH/CH2Cl2 to give the title compound as an off-white amorphous solid. mp 104-109° C. LC-MS m/z 549 (M+H)+, 1.65 min (ret time).

Workup

  1. customchromatographed on silica gel (10 g)
  2. washeluted with CH2Cl2 to 6:1:0.1, CH2Cl2
  3. customwas removed
  4. filtrationby filtering through a silica gel plug with 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-7338c3cc1f814290a7ad156abff438a2
Source dataset
uspto-grants-2010_03
Patent number
US07678801B2

Reaction notes

Loading…