Sodium Bicarbonate → HCID 178424638, compound

HRID 1851301Notes

Reaction equation

HRID 1851301 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][CH:23]=[CH:22][C:21]=1[C:26]1[C:27]([C:35]2[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=2)=[N:28][C:29]2[N:30]([CH:32]=[CH:33][N:34]=2)[CH:31]=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:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[C:27]([C:35]2[CH:36]=[CH:37][C:38]([CH2:39][N:16]3[CH2:17][CH2:18][CH:13]([C:11]4[N:12]=[C:8]([C:4]5[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=5)[NH:9][N:10]=4)[CH2:14][CH2:15]3)=[CH:41][CH:42]=2)=[N:28][C:29]2[N:30]([CH:32]=[CH:33][N:34]=2)[CH:31]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867030224-[6-(2-Fluorophenyl)-imidazo[1,2-a]pyrimidin-7-yl]-benzaldehydeHCID 178424635HCID 178424635, compound

Product 1

HCID 178424638HCID 178424638, compoundYield 20.3%

Reagents, catalysts & solvents 3

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

Procedure

398.6 mg (1.26 mmol) 2-Methyl-6-(5-piperidine-4-yl-2H-[1,2,4]triazole-3-yl)pyridine×2HCl are dissolved in 10.9 mL NMP. After addition of 0.42 mL triethylamine the reaction mixture is stirred for one hour. 400 mg (1.26 mmol) 4-[6-(2-Fluorophenyl)-imidazo[1,2-a]pyrimidin-7-yl]-benzaldehyde and 0.13 mL acetic acid are added. The reaction mixture is stirred over night at room temperature. 293.9 mg (1.39 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 22 hours. The reaction mixture is treated with saturated NaHCO3 and stirred for 60 minutes. The precipitate is filtered off, washed with water, dried and purified by HPLC yielding 139.1 mg (19.3%) of the title compound.

Workup

  1. stirringThe reaction mixture is stirred over night at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 22 hours
  3. stirringstirred for 60 minutes
  4. filtrationThe precipitate is filtered off
  5. washwashed with water
  6. customdried
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-54ba4e8338834b0f8e6a94459efed8a3
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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