Benzyl Alcohol → HCID 44626119, compound

HRID 533173Notes

Reaction equation

HRID 533173 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:12]1[N:17]=[CH:16][C:15]([C:18]2[N:23]3[N:24]=[C:25]([NH:27][C:28]([CH:30]4[CH2:32][CH2:31]4)=[O:29])[N:26]=[C:22]3[CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1>C1COCC1>[CH2:1]([O:8][C:12]1[N:17]=[CH:16][C:15]([C:18]2[N:23]3[N:24]=[C:25]([NH:27][C:28]([CH:30]4[CH2:31][CH2:32]4)=[O:29])[N:26]=[C:22]3[CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 58374744HCID 58374744, compound

Product 1

HCID 44626119HCID 44626119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

At 0° C. and under N2 atmosphere, benzyl alcohol (2 eq) in a solution of THF was treated with NaH 60% in mineral oil (4 eq) for 30 min. Then cyclopropanecarboxylic acid [5-(6-chloro-pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amide prepared by method A was added to the solution and the mixture was stirred at 70° C. for 3 hours. The reaction was completed. The reaction mixture was quenched with water and the compound was extracted with EtOAc. The compound was washed with brine, dried on MgSO4, filtrated and concentrated. Compound was purified on Prep HPLC.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionthe compound was extracted with EtOAc
  3. washThe compound was washed with brine
  4. customdried on MgSO4
  5. filtrationfiltrated
  6. concentrationconcentrated
  7. customCompound was purified on Prep HPLC

Sources & evidence

ORD record
ord-9a4194f6f5d74901934015a499d3cbef
Source dataset
uspto-grants-2014_10
Patent number
US08853240B2

Reaction notes

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