Acetic Acid → HCID 178482058, compound

HRID 1851307Notes

Reaction equation

HRID 1851307 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][C:24]1[N:25]=[C:26]2[N:31]=[C:30]([C:32]3[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=3)[C:29]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[C:28]([NH:46][CH3:47])[N:27]2[CH:48]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN1C(=O)CCC1>[CH3:47][NH:46][C:28]1[N:27]2[CH:48]=[C:24]([CH3:23])[N:25]=[C:26]2[N:31]=[C:30]([C:32]2[CH:39]=[CH:38][C:35]([CH2:36][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:34][CH:33]=2)[C:29]=1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 687522842-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridineHCID 867030554-(2-Methyl-5-methylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)benzaldehyde

Product 1

HCID 178482058HCID 178482058, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

237.8 mg (0.87 mmol) 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 6.8 mL NMP. 0.24 mL (1.74 mmol) triethylamine are added and the reaction mixture is stirred for one hour. 270 mg (0.79 mmol) 4-(2-Methyl-5-methylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde and 0.11 mL (1.89 mmol) acetic acid are added. The reaction mixture is stirred for two days at room temperature. 401.1 mg (1.89 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 9 days. After the usual work-up and purification by HPLC 29.6 mg (7.1%) of the desired title compound are obtained.

Workup

  1. stirringThe reaction mixture is stirred for two days at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 9 days
  3. customAfter the usual work-up and purification by HPLC 29.6 mg (7.1%) of the desired title compound
  4. customare obtained

Sources & evidence

ORD record
ord-18fb6d009c5540d68bb750d077dca58f
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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