1,3-Propanediamine → N-(2-amino-4-fluorophenyl)-6-(3-aminopropylamino)nicotinamide

HRID 1695042Notes

Reaction equation

HRID 1695042 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14](Cl)=[N:13][CH:12]=1.[CH2:19]([NH2:23])[CH2:20][CH2:21][NH2:22]>>[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([NH:22][CH2:21][CH2:20][CH2:19][NH2:23])=[N:13][CH:12]=1

Participants

3

Reactant 2

HCID 4281,3-PropanediamineHCID 57993734N-(2-amino-4-fluorophenyl)-6-chloronicotinamide

Product 1

HCID 57993745N-(2-amino-4-fluorophenyl)-6-(3-aminopropylamino)nicotinamideYield 52%

Procedure

N-(2-amino-4-fluorophenyl)-6-chloronicotinamide (266 mg, 1 mmol) and 6 ml of 1,3-propanediamine were heated to 80° C. for 3 hours. The excess 1,3-propanediamine was removed under vacuum. To the residue was added 5 ml of 0.20 M NaOH. The mixture was extracted with 100 ml of ethyl acetate. The ethyl acetate was removed under vacuum to give the title compound (158 mg, 52% yield) as a brown solid. LC-MS (m/z) 304 (M+1).

Workup

  1. customThe excess 1,3-propanediamine was removed under vacuum
  2. additionTo the residue was added 5 ml of 0.20 M NaOH
  3. extractionThe mixture was extracted with 100 ml of ethyl acetate
  4. customThe ethyl acetate was removed under vacuum

Sources & evidence

ORD record
ord-36e25e93bba24dd6a4e16d7de5f56383
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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