Cyclopropylamine → 6-Bromo-N-cyclopropyl-2-naphthalenecarboxamide

HRID 724203Notes

Reaction equation

HRID 724203 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.Cl.C(N=C=N[CH2:21][CH2:22][CH2:23][N:24](C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.C1(N)CC1>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:24][CH:23]1[CH2:21][CH2:22]1)=[O:14])[CH:6]=[CH:5]2

Participants

8

Reactant 5

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 218796186-Bromo-N-cyclopropyl-2-naphthalenecarboxamideYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Bromo-2-naphthoic acid (1.01 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.92 g) and 1-hydroxy-1H-benzotriazole monohydrate (0.735 g; HOBt) were dissolved in dimethylformamide (16 ml) under an argon atmosphere. N-Ethyldiisopropylamine (0.62 g) was added with stirring under ice-cooling. Cyclopropylamine (0.37 g) was added and the mixture was stood with stirring at room temperature for 18 h. The reaction mixture was poured into ethyl acetate (0.15 L) and the mixture was washed successively with water and saturated brine. The mixture was dried over anhydrous sodium sulfate and the solvent was concentrated. The precipitated crystals were collected by filtration and dried to give the title compound (0.817 g) as colorless needle crystals.

Workup

  1. temperaturecooling
  2. stirringwith stirring at room temperature for 18 h
  3. washthe mixture was washed successively with water and saturated brine
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. concentrationthe solvent was concentrated
  6. filtrationThe precipitated crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-51a367fb97a947cc92917363d1a065c2
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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