Sodium Bicarbonate → HCID 178424639, compound

HRID 1851299Notes

Reaction equation

HRID 1851299 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[NH:9][N:10]=[C:11]([CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[N:12]=2)[N:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:27]([C:35]3[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=3)=[N:28][C:29]3[N:30]([CH:32]=[CH:33][N:34]=3)[CH:31]=2)=[CH:22][CH:21]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CN1C(=O)CCC1.C(O)(=O)C.C(N(CC)CC)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[C:27]([C:35]3[CH:42]=[CH:41][C:38]([CH2:39][N:16]4[CH2:17][CH2:18][CH:13]([C:11]5[N:12]=[C:8]([C:4]6[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=6)[NH:9][N:10]=5)[CH2:14][CH2:15]4)=[CH:37][CH:36]=3)=[N:28][C:29]3[N:30]([CH:32]=[CH:33][N:34]=3)[CH:31]=2)=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867030204-[6-(4-Fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl]-benzaldehydeHCID 178424635HCID 178424635, compound

Product 1

HCID 178424639HCID 178424639, compoundYield 67.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8471TriethylamineSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

219 mg (0.69 mmol) 2-Methyl-6-(5-piperidine-4-yl-2H-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 5.4 mL NMP. After addition of 0.2 mL triethylamine the reaction mixture is stirred for one hour. 200 mg (0.63 mmol) 4-[6-(4-Fluorophenyl)imidazo[1,2-a]pyrimidin-7-yl]-benzaldehyde and 0.06 mL acetic acid are added. The reaction mixture is stirred over night at room temperature. 147 mg (0.69 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is treated with saturated NaHCO3 and stirred for 20 minutes. The precipitate is filtered off, washed with water and dried. 233 mg (62.6%) of the desired product are obtained. 100 mg of this material are further purified by HPLC yielding 74.3 mg of the title compound as formiate.

Workup

  1. stirringThe reaction mixture is stirred over night at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 18 hours
  3. stirringstirred for 20 minutes
  4. filtrationThe precipitate is filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-a78cd7ae3e7d43839fbf7172519c2e27
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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