Putrescine → N-(2-amino-4-fluorophenyl)-6-(4-aminobutylamino)nicotinamide

HRID 1695045Notes

Reaction equation

HRID 1695045 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]([NH2:24])[CH2:20][CH2:21][CH2:22][NH2:23]>>[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:23][CH2:22][CH2:21][CH2:20][CH2:19][NH2:24])=[N:13][CH:12]=1

Participants

3

Reactant 2

HCID 1045PutrescineHCID 57993734N-(2-amino-4-fluorophenyl)-6-chloronicotinamide

Product 1

HCID 57993725N-(2-amino-4-fluorophenyl)-6-(4-aminobutylamino)nicotinamideYield 47%

Procedure

N-(2-Amino-4-fluorophenyl)-6-chloronicotinamide (266 mg, 1 mmol) and 7 ml of 1,4-butanediamine were heated to 80° C. for 3 hours. The excess 1,4-butanediamine 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 (149 mg, 47% yield) as a brown solid. LC-MS (m/z) 318 (M+1).

Workup

  1. customThe excess 1,4-butanediamine 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-ae89f94e8fa441388c6816d82102be86
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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