Benzyl Alcohol → HCID 44626119, compound

HRID 885643Notes

Reaction equation

HRID 885643 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-bfc98cfa6e8d4e84a886d11f32624ef9
Source dataset
uspto-grants-2012_08
Patent number
US08242274B2

Reaction notes

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