1,3-Propanediamine → HCID 11201615, compound

HRID 917772Notes

Reaction equation

HRID 917772 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([I:31])[CH:28]=[CH:27][C:3]=1[NH:4][C:5]1[C:6]([C:13]([O:15]C2C(F)=C(F)C(F)=C(F)C=2F)=O)=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1.[CH2:32]([NH2:36])[CH2:33][CH2:34][NH2:35]>C1COCC1>[NH2:35][CH2:34][CH2:33][CH2:32][NH:36][C:13]([C:6]1[C:5]([NH:4][C:3]2[CH:27]=[CH:28][C:29]([I:31])=[CH:30][C:2]=2[F:1])=[CH:10][C:9](=[O:11])[N:8]([CH3:12])[CH:7]=1)=[O:15]

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 23631099HCID 23631099, compound

Product 1

HCID 11201615HCID 11201615, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,3,4,5,6-pentafluorophenyl 4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (0.20 g, 0.4 mmol) in THF (5 ml) was added to 1,3-propanediamine (0.35 ml, >10 eq) in THF (5 ml) and stirred at RT for 15 h. The solution was then concentrated under reduced pressure and the residue dissolved in 5% MeOH/EtOAc. The organic phase was washed with water, brine, dried (Na2SO4) and concentrated to give crude N-(3-aminopropyl)-4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide which was then recrystallised (MeOH/Hexane/EtOAc) (0.04 g, 22%); m.p. 201-206° C. 1H NMR [400 MHz, (CD3)2SO] δ 8.42 (br s, 1H), 8.25 (s, 1H), 7.74 (dd, J=10.2, 1.9 Hz, 1H), 7.57 (dt, J=8.5, 0.9 Hz, 1H), 7.29 (t, J=8.5 Hz, 1H), 5.60 (d, J=0.9 Hz, 1H), 3.38 (s, 3 H, obscured), 3.3-3.25 (m, 2 H, obscured), 2.81 (t, J=7.4 Hz, 2H), 1.75 (p, J=7.4 Hz, 2H). HPLC 94.4% (254 nm). HRMS (FAB+) calcd for C16H19FIN4O2 445.0537 (M+), found 445.0543.

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. dissolutionthe residue dissolved in 5% MeOH/EtOAc
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7d837f99d1d14e92b4551355bcd3f9e9
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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