1-Hydroxybenzotriazole → HCID 71287832, compound

HRID 83516Notes

Reaction equation

HRID 83516 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=3)=[CH:10][C:9]([NH2:21])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:22]=[C:23]1[NH:28][CH2:27][CH:26]([C:29](O)=[O:30])[CH2:25][CH2:24]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>O1CCCC1.O>[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=3)=[CH:10][C:9]([NH:21][C:29]([CH:26]3[CH2:25][CH2:24][C:23](=[O:22])[NH:28][CH2:27]3)=[O:30])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 5600906-Oxopiperidine-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 712877391-Phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine

Product 1

HCID 71287832HCID 71287832, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine (56 mg) in tetrahydrofuran (1.5 ml) were sequentially added an optically active compound of 6-oxopiperidine-3-carboxylic acid (43 mg) synthesized in Preparation 7 (derived from the low-polarity component of 5-((R)-4-benzyl-2-oxoxazolidine-3-carbonyl)-1-(2,4-dimethoxybenzyl)piperidin-2-one), HOBt.H2O (46 mg) and WSC.HCl (58 mg), and the mixture was stirred at room temperature overnight. To this reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The separated organic layer was concentrated under reduced pressure, the resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1) to give the titled compound (50 mg).

Workup

  1. customsynthesized in Preparation 7 (
  2. extractionthe mixture was extracted with ethyl acetate
  3. concentrationThe separated organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel thin-layer chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-6003fbbf4e7d48478a365bde9ed191ca
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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