Dichloromethane → HCID 19906401, compound

HRID 2371803Notes

Reaction equation

HRID 2371803 reaction equation
[C:1]([CH:4]([CH3:29])[CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[C:13]2[CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=2[O:27][CH3:28])=[CH:8][CH:7]=1)(O)=[O:2].Cl.C[N:32](C)[CH2:33][CH2:34][CH2:35]N=C=NCC.C(N)CC.C(Cl)Cl>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH2:33]([NH:32][C:1]([CH:4]([CH3:29])[CH2:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[C:13]2[CH2:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=2[O:27][CH3:28])=[CH:8][CH:7]=1)=[O:2])[CH2:34][CH3:35]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7852PropylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19906412HCID 19906412, compound

Product 1

HCID 19906401HCID 19906401, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-[7-(2-carboxypropyl)naphth-1-ylmethyl]-3-methoxybenzoate (1.176 g), 4-dimethylaminopyridine (440 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (690 mg), propylamine (0.295 ml) and methylene chloride (20 ml) was stirred for 18 h. Ethyl acetate (100 ml) was added, the solution was washed (1N hydrochloric acid, brine) and dried (MgSO4). Evaporation and flash chromatography, eluting with 2:30:70 triethylamine:ethyl acetate:petroleum ether, gave a solid. Recrystallization from methylene chloride and hexane, followed by grinding to a powder and vacuum drying, afforded methyl 4-[7-[2-(propylcarbamoyl)propyl]naphth-1-ylmethyl]-3-methoxybenzoate (910 mg, 70%) as a colorless solid; mp 129.5°-130.0° C.; MS(CI), m/e=434(M+H).

Workup

  1. washthe solution was washed (1N hydrochloric acid, brine)
  2. dry with materialdried (MgSO4)
  3. customEvaporation and flash chromatography
  4. washeluting with 2:30:70 triethylamine
  5. customethyl acetate:petroleum ether, gave a solid
  6. customRecrystallization from methylene chloride and hexane
  7. customby grinding to a powder and vacuum
  8. customdrying

Sources & evidence

ORD record
ord-6a5f6dedb3e84889a4b00970aab78ce4
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

Loading…