2-Methylbenzylamine → HCID 483318, compound

HRID 1383399Notes

Reaction equation

HRID 1383399 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=O.C(N(CC)CC)C.C(OC(Cl)=O)(C)C.[CH3:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32]>C1COCC1.C(Cl)Cl.CCOC(C)=O>[CH3:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH:32][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[N:7][CH:6]=2)[N:1]=1)=[O:13]

Participants

8

Reactant 4

HCID 69932-MethylbenzylamineHCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 7359081,6-Naphthyridine-2-carboxylic acid

Product 1

HCID 483318HCID 483318, compoundYield 37.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring mixture of 2-[1,6]naphthyridinecarboxylic acid (50 mg, 0.287 mmol), in anhydrous THF (5 ml) at 0° C. was added triethylamine (44 ml, 0.316 mmol). After 5 min, isopropylchloroformate (0.316 ml, 1M solution in toluene, 0.316 mmol) was added. The mixture was stirred at 0° C. for 20 min. then 2-methylbenzylamine (53.46 ml, 0.43 mmol) was added to the mixture at 0° C. The resulting mixture was allowed to warm to room temperature and stirred at room temperature for 5 h then diluted in CH2Cl2 (100 ml). The organic layer was washed with water, dried over anhydrous MgSO4, and concentrated to give the crude mixture. Chromatography of the crude (Hex:EtOAc=1:1 to pure EtOAc) afforded desired product as white solid (29.8 mg, 37%): m.p. 120-121° C.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for 5 h
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customto give the crude mixture

Sources & evidence

ORD record
ord-ef5afbf807f7450a90afe3bfb700165a
Source dataset
uspto-grants-2001_07
Patent number
US06255318B1

Reaction notes

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