1-Hydroxybenzotriazole → HCID 18976209, compound

HRID 2393590Notes

Reaction equation

HRID 2393590 reaction equation
Cl.CN(C)CCCN=C=NCC.Cl.[NH2:14][CH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:16]1=[O:29].[CH2:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32][CH:31]1[C:40](O)=[O:41].ON1C2C=CC=CC=2N=N1>C(N(CC)CC)C.C(Cl)Cl>[O:29]=[C:16]1[CH:15]([NH:14][C:40]([CH:31]2[CH2:32][CH2:33][C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:30]2)=[O:41])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]1[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1013701,2,3,4-Tetrahydro-2-naphthoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18976150HCID 18976150, compound

Product 1

HCID 18976209HCID 18976209, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Under ice cooling, 1.10 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride was added to a stirred mixture of 1.22 g of 3-amino-2,3-dihydro-1-pentyl-1H-indol-2-one hydrochloride, 0.93 g of 1,2,3,4-tetrahydronaphthalene-2-carboxylic acid, 0.72 g of 1-hydroxybenzotriazole and 40 ml of methylene chloride. After the reaction mixture was stirred under ice cooling for 1 hour, 1.0 ml of triethylamine was added to the mixture. The resulting mixture was stirred under ice cooling for 2 hours and then stirred at room temperature for 2 hours. The solvent was removed by evaporation under reduced pressure. The residue was extracted with ethyl acetate, and the extract was washed and dried. After removal of solvent, the residual solid was recrystallized from ethyl acetate-hexane to afford 1.36 g of N-(2,3-dihydro-2-oxo-1-pentyl-1H-indol-3-yl)-1,2,3,4-tetrahydronaphthalene-2-carboxamide as colorless crystals. Melting point: 127° to 132° C., IR (Nujol) (cm-1): 3280, 1725, 1640, 1610, MS (m/z): 376 (M+), 218 (base), 147, 31.

Workup

  1. stirringThe resulting mixture was stirred under ice cooling for 2 hours
  2. stirringstirred at room temperature for 2 hours
  3. customThe solvent was removed by evaporation under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe extract was washed
  6. customdried
  7. customAfter removal of solvent
  8. customthe residual solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-57c7ca4161c945328ec46f4abe9b3bf8
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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