Sodium Bicarbonate → HCID 178432375, compound

HRID 1851295Notes

Reaction equation

HRID 1851295 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N: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)[CH:3]=1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[C:27]1[C:28]([C:37]2[CH:44]=[CH:43][C:40]([CH:41]=O)=[CH:39][CH:38]=2)=[N:29][C:30]2[N:31]([N:33]=[C:34]([CH3:36])[N:35]=2)[CH:32]=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>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[NH:9][N:10]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:41][C:40]4[CH:39]=[CH:38][C:37]([C:28]5[C:27]([C:21]6[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=6[F:19])=[CH:32][N:31]6[N:33]=[C:34]([CH3:36])[N:35]=[C:30]6[N:29]=5)=[CH:44][CH:43]=4)[CH2:15][CH2:14]3)[N:12]=2)[CH:3]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 867030514-[6-(2,4-Difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehydeHCID 178478250HCID 178478250, compound

Product 1

HCID 178432375HCID 178432375, compound

Reagents, catalysts & solvents 3

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

Procedure

192 mg (0.57 mmol) 4-Chloro-2-(5-piperidine-4-yl-2H-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 4.8 mL NMP. After addition of 0.19 mL triethylamine the reaction mixture is stirred for one hour. 200 mg (0.57 mmol) 4-[6-(2,4-Difluorophenyl)-2-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]-benzaldehyde and 0.06 mL acetic acid are added. The reaction mixture is stirred over night at room temperature. 133 mg (0.63 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 5 hours. The reaction mixture is treated with saturated NaHCO3. The precipitate is filtered off, washed with water and dried. After chromatography of the precipitate on silica gel (dichloromethane/methanol) 99.1 mg (27.6%) 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 5 hours
  3. filtrationThe precipitate is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-cfaad6cb63014a1b8ddfda59dd95a70b
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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