Sodium Bicarbonate → HCID 178424640, compound

HRID 1851294Notes

Reaction equation

HRID 1851294 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:21]=[C:22]([C:26]2[C:27]([C:36]3[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=3)=[N:28][C:29]3[N:30]([N:32]=[C:33]([CH3:35])[N:34]=3)[CH:31]=2)[CH:23]=[CH:24][CH:25]=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]=[C:22]([C:26]2[C:27]([C:36]3[CH:37]=[CH:38][C:39]([CH2:40][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:42][CH:43]=3)=[N:28][C:29]3[N:30]([N:32]=[C:33]([CH3:35])[N:34]=3)[CH:31]=2)[CH:23]=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867030534-[6-(3-Fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehydeHCID 178424635HCID 178424635, compound

Product 1

HCID 178424640HCID 178424640, compound

Reagents, catalysts & solvents 3

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

Procedure

323 mg (1.02 mmol) 2-Methyl-6-(5-piperidine-4-yl-2H-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 8.8 mL NMP. After addition of 0.34 mL triethylamine the reaction mixture is stirred for two hours. 340 mg (1.02 mmol) 4-[6-(3-Fluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde and 0.1 mL acetic acid are added. The reaction mixture is stirred over night at room temperature. 251 mg (1.12 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 6 hours. The reaction mixture is treated with saturated NaHCO3. The precipitate is filtered off, washed with water and dried. After purification by preparative HPLC 13.2 mg (2.3%) of the desired product are obtained.

Workup

  1. stirringThe reaction mixture is stirred over night at room temperature
  2. stirringthe reaction mixture is stirred at room temperature for 6 hours
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. customdried
  6. customAfter purification by preparative HPLC 13.2 mg (2.3%) of the desired product
  7. customare obtained

Sources & evidence

ORD record
ord-b7ae6ca73b4e4f8fbc227aa74cbc0657
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

Loading…