Acetic Acid → HCID 178429817, compound

HRID 1851309Notes

Reaction equation

HRID 1851309 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][CH:47]([CH3:49])[CH3:48])[N:27]2[CH:50]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN1C(=O)CCC1>[CH:47]([NH:46][C:28]1[N:27]2[CH:50]=[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:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([CH3:49])[CH3:48]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 687522842-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridineHCID 867030574-(2-Methyl-5-isopropylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde

Product 1

HCID 178429817HCID 178429817, compoundYield 1.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

227.9 mg (0.83 mmol) 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 6.5 mL NMP. 0.25 mL (1.8 mmol) triethylamine are added and the reaction mixture is stirred for one hour. 280 mg (0.76 mmol) 4-(2-Methyl-5-isopropylamino-6-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-benzaldehyde and 0.08 mL (1.36 mmol) acetic acid are added. The reaction mixture is stirred for three days at room temperature. 176.2 mg (0.83 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 18 hours. Additional 88 mg NaBH(OAc)3 are added and stirring is continued for 26 hours. After the usual work-up and purification by column chromatography and by HPLC 4.9 mg (1.1%) of the desired title compound are obtained.

Workup

  1. stirringThe reaction mixture is stirred for three days at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 18 hours
  3. stirringstirring
  4. waitis continued for 26 hours
  5. customAfter the usual work-up and purification by column chromatography

Sources & evidence

ORD record
ord-48b27eda5dca4899b291006fb33aeae7
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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