Acetic Acid → HCID 178424646, compound

HRID 1851312Notes

Reaction equation

HRID 1851312 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[NH:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=3)[N:6]=2)[CH2:2]1.C(N(CC)CC)C.[CH:24]([NH:27][C:28]1[N:33]2[N:34]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[N:36]=[C:32]2[N:31]=[C:30]([C:43]2[CH:50]=[CH:49][C:46]([CH:47]=O)=[CH:45][CH:44]=2)[C:29]=1[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([CH3:26])[CH3:25].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[CH:24]([NH:27][C:28]1[N:33]2[N:34]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[N:36]=[C:32]2[N:31]=[C:30]([C:43]2[CH:44]=[CH:45][C:46]([CH2:47][N:1]3[CH2:4][CH:3]([C:5]4[N:6]=[C:7]([C:10]5[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=5)[NH:8][N:9]=4)[CH2:2]3)=[CH:49][CH:50]=2)[C:29]=1[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([CH3:26])[CH3:25]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 687534852-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridineHCID 86703059HCID 86703059, compound

Product 1

HCID 178424646HCID 178424646, compoundYield 2.54%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

138.8 mg (0.51 mmol) 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridine×2HCl (60% pure) are dissolved in 3.9 mL NMP. 0.15 mL (1.08 mmol) triethylamine are added and the reaction mixture is stirred for one hour. 200 mg (0.46 mmol) 4-(7-Isopropylamino-6-phenyl-2-pyridine-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde and 0.05 mL (0.83 mmol) acetic acid are added. The reaction mixture is stirred over night at room temperature. 107 mg (0.51 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature over night. The reaction mixture is treated with NaHCO3 and the formed precipitate has been filtered off. The filtrate is extracted with methyl-tert.butylether. The organic phase is washed with water, dried (Na2SO4) and the solvent removed. This residue and the precipitate are combined and purified by column chromatography (silicagel, eluents: dichloromethane/methanol) and additionally by HPLC yielding 7.4 mg (2.54%) of the desired compound.

Workup

  1. stirringThe reaction mixture is stirred over night at room temperature
  2. stirringthe reaction mixture is stirred at room temperature over night
  3. filtrationthe formed precipitate has been filtered off
  4. extractionThe filtrate is extracted with methyl-tert.butylether
  5. washThe organic phase is washed with water
  6. dry with materialdried (Na2SO4)
  7. customthe solvent removed
  8. custompurified by column chromatography (silicagel, eluents: dichloromethane/methanol) and additionally by HPLC

Sources & evidence

ORD record
ord-8d981fdedcbb4d4493fa24794f2189a1
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

Loading…