1-Hydroxybenzotriazole → HCID 71287849, compound

HRID 83524Notes

Reaction equation

HRID 83524 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.[C:22]([O:26][C:27]([NH:29][C@H:30]([CH2:34][NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:31](O)=[O:32])=[O:28])([CH3:25])([CH3:24])[CH3:23].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[C:39]([O:38][C:36](=[O:37])[NH:35][CH2:34][C@@H:30]([NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[C:31](=[O:32])[NH:21][C:9]1[CH:10]=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH3:20])[CH:13]=2)[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1)([CH3:42])([CH3:41])[CH3:40]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18631841HCID 18631841, compoundHCID 712877391-Phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine

Product 1

HCID 71287849HCID 71287849, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-phenyl-5-(3-propylphenyl)-1H-pyrazol-3-ylamine (177 mg) prepared according to the same procedures as Preparation 8 in DMF (1.8 ml) were added (R)-2,3-bis-tert-butoxycarbonylaminopropionic acid (292 mg), HOBt.H2O (147 mg) and WSC.HCl (184 mg), and the mixture was stirred at room temperature for 2 hours. To this reaction solution were added water and a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to give the titled compound (329 mg).

Workup

  1. extractiona saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate
  2. washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-2194849e7b6b40d08209eea378b93701
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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