3-[6-Chloro-2-(ethylamino)-3-pyridinyl]-2-cyano-3-hydroxy-N-methyl-2-propenamide → 2-Amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide

HRID 2088857Notes

Reaction equation

HRID 2088857 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([C:11]([OH:19])=[C:12]([C:17]#[N:18])[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1>C(O)CCC>[NH2:18][C:17]1[N:8]([CH2:9][CH3:10])[C:6]2[C:5]([C:11](=[O:19])[C:12]=1[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=2

Participants

3

Reactant 1

HCID 866423353-[6-Chloro-2-(ethylamino)-3-pyridinyl]-2-cyano-3-hydroxy-N-methyl-2-propenamide

Product 1

HCID 866423362-Amino-7-chloro-1-ethyl-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamideYield 57%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 19.0 g (49.8 mmol) of the crude product obtained from step 1.4 in 600 ml of n-butanol is heated for 48 hours at 110° C. The solvent is evaporated off under reduced pressure and the solid obtained is triturated in methanol. The solid is then filtered off and oven-dried. 7.9 g of the expected product are obtained in the form of a pale yellow solid. Yield=57%. Melting point: 283-286° C. MH+: 281.2 (tr=6.99 min., condition 1).

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. customthe solid obtained
  3. customis triturated in methanol
  4. filtrationThe solid is then filtered off
  5. customoven-dried

Sources & evidence

ORD record
ord-ffc527f01eb845bca3b899abf7269d03
Source dataset
uspto-grants-2013_05
Patent number
US08436011B2

Reaction notes

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