Triethylamine → HCID 86710531, compound

HRID 873328Notes

Reaction equation

HRID 873328 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:17])[C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[CH:25]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]1>C(Cl)Cl>[Br:1][C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH:17][C:28]([CH:25]3[CH2:27][CH2:26]3)=[O:29])[C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 70980308HCID 70980308, compound

Product 1

HCID 86710531HCID 86710531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Bromo-3-phenyl-pyrazolo[1,5-a]pyridin-2-ylamine (0.295 g 1 eq) was dissolved in DCM (3 mL) at 5° C. and Et3N (356 μL) was added followed by the cyclopropane carbonyl chloride (234 μL). The reaction mixture was then allowed to warm to room temperature. The solvent was removed in vacuo the residue was treated with 7 M methanolic ammonia solution (5 mL) and stirred at room temp for 1 h to hydrolyse any bis-acylated product. The solvent was removed in vacuo and the residue was re-dissolved in DCM and washed with water and brine. The organics were passed through a hydrophobic frit and concentrated in vacuo. Purification by preparative HPLC

Workup

  1. customThe solvent was removed in vacuo the residue
  2. additionwas treated with 7 M methanolic ammonia solution (5 mL)
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was re-dissolved in DCM
  5. washwashed with water and brine
  6. concentrationconcentrated in vacuo
  7. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-e4a8614377b14cb0aa21bca3d060c144
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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