Acetic Acid → HCID 178482059, compound

HRID 1851305Notes

Reaction equation

HRID 1851305 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]=[CH:12][N:11]=3)[N:6]=2)[CH2:2]1.C(N(CC)CC)C.[CH3:23][NH:24][C:25]1[N:30]2[CH:31]=[CH:32][N:33]=[C:29]2[N:28]=[C:27]([C:34]2[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=2)[C:26]=1[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[CH3:23][NH:24][C:25]1[N:30]2[CH:31]=[CH:32][N:33]=[C:29]2[N:28]=[C:27]([C:34]2[CH:41]=[CH:40][C:37]([CH2:38][N:1]3[CH2:4][CH:3]([C:5]4[N:6]=[C:7]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=5)[NH:8][N:9]=4)[CH2:2]3)=[CH:36][CH:35]=2)[C:26]=1[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 687522842-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridineHCID 866306614-(5-Methylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde

Product 1

HCID 178482059HCID 178482059, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

257 mg (0.94 mmol) 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 7.3 mL NMP. After addition of 0.26 mL (1.88 mmol) triethylamine the reaction mixture is stirred for one hour. 280 mg (0.85 mmol) 4-(5-Methylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde and 0.12 mL (2.05 mmol) acetic acid are added. The reaction mixture is stirred for 24 hours at room temperature. 469.9 mg (2.2 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 saturated NaHCO3. The precipitate is filtered off, washed with water, dried and purified by chromatography (silicagel, eluents: dichloromethane/methanol) yielding 163 mg (33.5%) of the desired title compound.

Workup

  1. stirringThe reaction mixture is stirred for 24 hours at room temperature
  2. stirringthe reaction mixture is stirred at room temperature over night
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. customdried
  6. custompurified by chromatography (silicagel, eluents: dichloromethane/methanol)

Sources & evidence

ORD record
ord-bdd0c5f4271c424b8d2bc6436e67f9e4
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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