Pyridine → HCID 178438463, compound

HRID 1412781Notes

Reaction equation

HRID 1412781 reaction equation
[O:1]=[C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:25][C:24](=[O:26])[O:23][N:22]=3)=[CH:11][CH:10]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[N:5]2[N:30]=[CH:31][N:32]=[C:4]2[N:3]1[C@H:33]1[CH2:38][CH2:37][C@H:36]([O:39][CH2:40][C:41]2([C:45]([NH2:47])=O)[CH2:44][CH2:43][CH2:42]2)[CH2:35][CH2:34]1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1.C(OCC)(=O)C>[O:1]=[C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]3[NH:25][C:24](=[O:26])[O:23][N:22]=3)=[CH:11][CH:10]=2)=[C:6]([CH2:27][CH2:28][CH3:29])[N:5]2[N:30]=[CH:31][N:32]=[C:4]2[N:3]1[C@H:33]1[CH2:34][CH2:35][C@H:36]([O:39][CH2:40][C:41]2([C:45]#[N:47])[CH2:44][CH2:43][CH2:42]2)[CH2:37][CH2:38]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 178438464HCID 178438464, compound

Product 1

HCID 178438463HCID 178438463, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (10 mL) of 1-[({trans-4-[5-oxo-6-{[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl]cyclohexyl}oxy)methyl]cyclobutanecarboxamide (0.22 g) and pyridine (0.11 mL) in tetrahydrofuran was added trifluoroacetic acid anhydride (0.093 mL) at 0° C., and the mixture was stirred for 30 min. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.15 g, 69%).

Workup

  1. washwashed with water
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5377fd98ae804844bbef0f6a41900cdf
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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