Ethylenediamine → N-(2-amino-4-fluorophenyl)-6-(2-aminoethylamino)nicotinamide

HRID 1695039Notes

Reaction equation

HRID 1695039 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]([NH2:22])[CH2:20][NH2:21]>>[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:21][CH2:20][CH2:19][NH2:22])=[N:13][CH:12]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 57993734N-(2-amino-4-fluorophenyl)-6-chloronicotinamide

Product 1

HCID 57993718N-(2-amino-4-fluorophenyl)-6-(2-aminoethylamino)nicotinamideYield 61%

Procedure

N-(2-Amino-4-fluorophenyl)-6-chloronicotinamide (266 mg, 1 mmol) and 5 ml of ethylenediamine were heated to 80° C. for 3 hours. The excess ethylenediamine 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 (176 mg, 61% yield) as a brown solid. LC-MS (m/z) 290 (M+1).

Workup

  1. customThe excess ethylenediamine 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-ae26a3f0e7b54ae884468544f9ba3493
Source dataset
uspto-grants-2012_04
Patent number
US08158656B2

Reaction notes

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