Water → HCID 22467377, compound

HRID 1934715Notes

Reaction equation

HRID 1934715 reaction equation
[C:1]([C:4]1[CH:28]=[CH:27][C:7]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=2[NH:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:6][CH:5]=1)([OH:3])=O.Cl.C[N:31](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.O>CN(C)C=O.N>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10](=[O:26])[C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=2[NH:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:27][CH:28]=1)(=[O:3])[NH2:31]

Participants

7

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22467351HCID 22467351, compound

Product 1

HCID 22467377HCID 22467377, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 222AmmoniaCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(4-carboxybenzyl)-2-(cyclopentylamino)-5-nitrobenzamide (120 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (90.0 mg) and 1-hydroxybenzotriazole (63.4 mg) in anhydrous dimethylformamide (2 mL) was stirred for an hour at ambient temperature. After addition of 28% ammonia solution (10 drops), the mixture was stirred for 15 hours at ambient temperature and poured into water. The resulting precipitates were collected by filtration, washed with water and purified by a silica gel column chromatography eluting with 10% methanol in chloroform. The obtained product was triturated with diisopropyl ether to give N-(4-carbamoylbenzyl)-2-(cyclopentylamino)-5-nitrobenzamide (107 mg) as yellow powders.

Workup

  1. stirringthe mixture was stirred for 15 hours at ambient temperature
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. custompurified by a silica gel column chromatography
  6. washeluting with 10% methanol in chloroform
  7. customThe obtained product was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-77a99d197401450bbb9c16a2c78e704e
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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