Pyridine → HCID 58968638, compound

HRID 2075049Notes

Reaction equation

HRID 2075049 reaction equation
[CH3:1][O:2][CH:3]([CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)[C:4]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:5]=1[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.N1C=CC=CC=1.[C:49](Cl)(=[O:51])[CH3:50]>C(Cl)Cl>[F:26][C:25]([F:28])([F:27])[C:17]1[CH:16]=[C:15]([CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=1)[CH2:14][N:7]([CH2:6][C:5]1[CH:29]=[C:30]([C:33]([F:36])([F:35])[F:34])[CH:31]=[CH:32][C:4]=1[CH:3]([O:2][CH3:1])[CH:37]1[CH2:38][CH2:39][N:40]([C:49](=[O:51])[CH3:50])[CH2:41][CH2:42]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 58968730HCID 58968730, compound

Product 1

HCID 58968638HCID 58968638, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-(methoxy piperidin-4-ylmethyl)-5-(trifluoromethyl)benzyl)-N-(3,5-bis(trifluoromethyl)benzyl)-2-methyl-2H-tetrazol-5-amine (20.5 mg, 0.034 mmol) in methylene chloride (0.5 mL) at room temperature was added pyridine (10 μL, 0.1 mmol) followed by acetyl chloride (5 μL, 0.07 mmol). The mixture was stirred at room temperature overnight. Solvent was removed in vacuo. The residue was purified by chromatography over 12+S Biotage silica column (eluted with 10-100% ethyl acetate in hexanes) to afford the title compound (14 mg, 64%). 1H NMR (400 MHz, CDCl3) δ ppm 1.17-1.34 (m, 3H) 1.69-1.78 (m, 1H) 1.87 (t, J=12.65 Hz, 1H) 2.04 (s, 1.5H) 2.06 (s, 1.5H) 2.27-2.41 (m, 1H) 2.82-2.93 (m, 1H) 3.04 (s, 3H) 3.72 (d, J=15.77 Hz, 0.5H) 3.81 (d, J=12.45 Hz, 0.5H) 4.18 (d, J=6.64 Hz, 1H) 4.21 (s, 3H) 4.54-4.65 (m, 1H) 4.65-4.73 (m, 3H) 4.87 (d, J=16.60 Hz, 1H) 7.37 (s, 1H) 7.50 (d, J=7.88 Hz, 1H) 7.59 (d, J=7.88 Hz, 1H) 7.64 (s, 2H) 7.78 (s, 1H). MS (ES+) Calc: 652.2, Found: 653.5 (M+1)

Workup

  1. customSolvent was removed in vacuo
  2. customThe residue was purified by chromatography over 12+S Biotage silica column (eluted with 10-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c561c1dc38b3421184b730f032e61da7
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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