Pyridine → HCID 178520623, compound

HRID 2214743Notes

Reaction equation

HRID 2214743 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O.[C:15]1([C:21]2[CH:22]=[C:23]3[C:29]([NH2:30])=[N:28][NH:27][C:24]3=[N:25][CH:26]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl.CN(C)C=O.CN(C)C1C=CN=CC=1>[Br-:7].[C:15]1([C:21]2[CH:22]=[C:23]3[C:29]([NH:30][C:12]([CH2:11][CH2:10][CH2:9][CH2:8][N+:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:14])=[N:28][NH:27][C:24]3=[N:25][CH:26]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 163685-Bromovaleric acidHCID 65578Oxalyl chlorideHCID 178509225HCID 178509225, compound

Product 1

HCID 178520623HCID 178520623, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.1 mL, 1.2 mmol) was added to a solution of 5-bromovaleric acid (86 mg, 0.48 mmol) in dichloromethane (10 mL). N,N-Dimethylformamide (1 drop) was added and the mixture was stirred at ambient temperature for 16 hours. The solvent was removed under vacuum, the residue was azeotroped with toluene (3×30 mL) and evaporated to dryness. To this crude acid chloride was added 5-phenyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine (Description 2; 100 mg, 0.48 mmol), pyridine (20 mL). and 4-dimethylaminopyridine (cat). The solution was refluxed at 120° C. for 16 hours then evaporated. The residual material was purified by preparative HPLC on a C18 column, using a gradient elution with 10–90% v/v of acetonitrile (containing 0.01% v/v trifluoroacetic acid) and water (containing 0.1% v/v trifluoroacetic acid) to afford the title compound.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was azeotroped with toluene (3×30 mL)
  3. customevaporated to dryness
  4. temperatureThe solution was refluxed at 120° C. for 16 hours
  5. customthen evaporated
  6. customThe residual material was purified by preparative HPLC on a C18 column
  7. washa gradient elution with 10–90% v/v of acetonitrile (
  8. additioncontaining 0.01% v/v trifluoroacetic acid) and water (
  9. additioncontaining 0.1% v/v trifluoroacetic acid)

Sources & evidence

ORD record
ord-7de5704063da43e3af6fe7d50f560c77
Source dataset
uspto-grants-2006_09
Patent number
US07109199B2

Reaction notes

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