Acetic Acid → HCID 178456712, compound

HRID 1851311Notes

Reaction equation

HRID 1851311 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.[CH:23]([NH:26][C:27]1[N:32]2[CH:33]=[CH:34][N:35]=[C:31]2[N:30]=[C:29]([C:36]2[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=2)[C:28]=1[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([CH3:25])[CH3:24].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN1C(=O)CCC1>[CH:23]([NH:26][C:27]1[N:32]2[CH:33]=[CH:34][N:35]=[C:31]2[N:30]=[C:29]([C:36]2[CH:43]=[CH:42][C:39]([CH2:40][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:38][CH:37]=2)[C:28]=1[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([CH3:25])[CH3:24]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 687522842-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridineHCID 86703058HCID 86703058, compound

Product 1

HCID 178456712HCID 178456712, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

253.8 mg (0.93 mmol) 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 7.2 mL NMP. 0.26 mL (1.85 mmol) triethylamine are added and the reaction mixture is stirred for one hour. 300 mg (0.84 mmol) 4-(5-Isopropylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde and 0.12 mL (2.02 mmol) acetic acid are added. The reaction mixture is stirred for 24 hours at room temperature. 463.8 mg (2.2 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature over night. After the usual work-up and purification by column chromatography (silicagel, eluents: dichloromethane/methanol) 132 mg (27.5%) of the pure title compound and 42 mg (9.2%) of the slightly contaminated title compound are obtained.

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. customAfter the usual work-up and purification by column chromatography (silicagel, eluents: dichloromethane/methanol) 132 mg (27.5%) of the pure title compound and 42 mg (9.2%) of the slightly contaminated title compound
  4. customare obtained

Sources & evidence

ORD record
ord-b87ee688edc14f80ad8666244578941f
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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