Morpholine → HCID 66633703, compound

HRID 1961483Notes

Reaction equation

HRID 1961483 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1)=[O:14])[C:6]([CH3:12])=[N:7]2.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C1COCC1>[CH3:12][C:6]1[C:5]([C:13]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)=[O:14])=[CH:4][C:3]2[C:8](=[N:9][CH:10]=[CH:11][C:2]=2[N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)[N:7]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 66745521HCID 66745521, compound

Product 1

HCID 66633703HCID 66633703, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Chloro-2-methyl-N-(3-(trifluoromethyl)benzyl)-1,8-naphthyridine-3-carboxamide (100 mg, 0.26 mmol) was dissolved in THF (10 ml) together with morpholine (45 μl, 0.52 mmol) and refluxed for 18 hours. The reaction was cooled and evaporated, the residue was purified by flash chromatography using CH2Cl2/CH3OH (20:1→10:1) as eluent to give 34 mg (30%) of 2-methyl-5-morpholino-N-(3-(trifluoromethyl)benzyl)-1,8-naphthyridine-3-carboxamide as a pale mass.

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureThe reaction was cooled
  3. customevaporated
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e1cd9cc0b47246c684921ef7a8864ada
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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