Pyridine → HCID 59437565, compound

HRID 2382906Notes

Reaction equation

HRID 2382906 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:17]2[CH:18]=[CH:19][C:20]3[N:21]([N:23]=[C:24]([NH2:26])[N:25]=3)[CH:22]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1C=CC=CC=1.[N:33]1([CH2:39][C:40]2[CH:48]=[CH:47][C:43]([C:44](Cl)=[O:45])=[CH:42][CH:41]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>ClCCl>[CH2:10]([O:9][C:8]1[CH:7]=[CH:6][C:5]([C:17]2[CH:18]=[CH:19][C:20]3[N:21]([N:23]=[C:24]([NH:26][C:44](=[O:45])[C:43]4[CH:47]=[CH:48][C:40]([CH2:39][N:33]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]5)=[CH:41][CH:42]=4)[N:25]=3)[CH:22]=2)=[CH:4][C:3]=1[O:2][CH3:1])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 13748936HCID 13748936, compoundHCID 59437518HCID 59437518, compound

Product 1

HCID 59437565HCID 59437565, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a reaction vessel containing the 6-{3-(methyloxy)-4-[(phenylmethyl)oxy]phenyl}[1,2,4]triazolo[1,5-a]pyridin-2-amine (104 mg, 0.3 mmol, 1 equivalent) and pyridine (0.063 mL, 1.2 mmol, 4 eq.) in dichloromethane (1 mL) was added 4-piperidin-1-ylmethyl-benzoyl chloride (142 mg, 0.6 mmol, 2 eq.) as a solution in dichloromethane (2 mL), dropwise. The vessel was capped and heated to reflux for approximately 16 hours. The reaction mixture was cooled and the solvent removed in vacuo. The residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give N-[6-(4-benzyloxy-3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-piperidin-1-ylmethyl-benzamide as a white solid (14.9 mg, 9%).

Workup

  1. customThe vessel was capped
  2. temperatureheated
  3. temperatureto reflux for approximately 16 hours
  4. temperatureThe reaction mixture was cooled
  5. customthe solvent removed in vacuo
  6. dissolutionThe residue dissolved in DMSO (1.5 mL)
  7. custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-1ab34c11d5b047a6b0082eb317082472
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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