2-Pyridinecarboxaldehyde → HCID 67005446, compound

HRID 563144Notes

Reaction equation

HRID 563144 reaction equation
[CH2:1]([C@H:8]([N:17]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:35][CH:34]=1)[C:18](=[O:31])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[C:9](=[O:16])[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[CH:50]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[CH2:1]([C@H:8]([N:17]([CH2:32][C:33]1[CH:34]=[CH:35][C:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:37][CH:38]=1)[C:18](=[O:31])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[C:9](=[O:16])[N:10]1[CH2:11][CH2:12][N:13]([CH2:50][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][N:44]=2)[CH2:14][CH2:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67005741HCID 67005741, compound

Product 1

HCID 67005446HCID 67005446, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N—((S)-1-Benzyl-2-oxo-2-piperazin-1-yl-ethyl)-N-(4-pentyl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide (50 mg, 0.084 mmol) was dissolved in acetonitrile (1 mL) and pyridine-2-carbaldehyde (10 mg, 0.092 mmol) and sodium triacetoxyborohydride (26.7 mg, 0.126 mmol) was added. The mixture was stirred at rt for 16 h, filtered and directly purified by prep. HPLC to give 29 mg of N—[(S)-1-Benzyl-2-oxo-2-(4-pyridin-2-ylmethyl-piperazin-1-yl)-ethyl]-N-(4-pentyl-benzyl)-3-(4-trifluoromethyl-phenyl)-acrylamide. LC-MS: tR=1.02 min; [M+H]+=683.58.

Workup

  1. filtrationfiltered
  2. customdirectly purified by prep

Sources & evidence

ORD record
ord-8f9f3428aae24285b3d21f8b041e374e
Source dataset
uspto-grants-2011_11
Patent number
US08067419B2

Reaction notes

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