Sodium Bicarbonate → HCID 178424636, compound

HRID 1851297Notes

Reaction equation

HRID 1851297 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.C1([C:22]2[CH:29]=[C:28]([C:30]3[C:35]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)=[CH:34][N:33]4[N:43]=[CH:44][N:45]=[C:32]4[N:31]=3)[CH:27]=[CH:26][C:23]=2[CH:24]=O)CC1.[BH-](O[C:56]([CH3:58])=O)(OC(C)=O)OC(C)=O.[Na+].[C:60]([O-])(O)=O.[Na+]>CN1C(=O)CCC1.C(O)(=O)C.C(N(CC)CC)C>[CH:58]1([C:44]2[N:45]=[C:32]3[N:31]=[C:30]([C:28]4[CH:29]=[CH:22][C:23]([CH2:24][N:16]5[CH2:17][CH2:18][CH:13]([C:11]6[N:12]=[C:8]([C:4]7[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[N:3]=7)[NH:9][N:10]=6)[CH2:14][CH2:15]5)=[CH:26][CH:27]=4)[C:35]([C:36]4[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=4)=[CH:34][N:33]3[N:43]=2)[CH2:56][CH2:60]1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867030522-Cyclopropyl-4-[6-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehydeHCID 178424635HCID 178424635, compound

Product 1

HCID 178424636HCID 178424636, compound

Reagents, catalysts & solvents 3

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

Procedure

154 mg (0.49 mmol) 2-Methyl-6-(5-piperidine-4-yl-2H-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 4.2 mL NMP. After addition of 0.16 mL triethylamine the reaction mixture is stirred for one hour. 350 mg (50% pure) 2-Cyclopropyl-4-[6-(4-fluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde and 0.05 mL acetic acid are added. The reaction mixture is stirred over night at room temperature. 113 mg (0.54 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. After chromatography of the precipitate on silica gel (dichloromethane/methanol) 192.2 mg (63.8%) 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 18 hours
  3. stirringstirred for 20 minutes
  4. filtrationThe precipitate is filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-c33aa09a4b004be08ecfa1bbe94b705f
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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