Sodium Bicarbonate → HCID 178498893, compound

HRID 1851278Notes

Reaction equation

HRID 1851278 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[NH:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=3)[N:6]=2)[CH2:2]1.[CH3:17][O:18][C:19]([C:21]1[CH:22]=[N:23][N:24]2[CH:29]=[C:28]([C:30]3[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=3[F:37])[C:27]([C:38]3[CH:43]=[CH:42][C:41]([CH:44]=O)=[CH:40][CH:39]=3)=[N:26][C:25]=12)=[O:20].[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>[CH3:17][O:18][C:19]([C:21]1[CH:22]=[N:23][N:24]2[CH:29]=[C:28]([C:30]3[C:31]([F:37])=[CH:32][CH:33]=[CH:34][C:35]=3[F:36])[C:27]([C:38]3[CH:39]=[CH:40][C:41]([CH2:44][N:1]4[CH2:4][CH:3]([C:5]5[N:6]=[C:7]([C:10]6[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=6)[NH:8][N:9]=5)[CH2:2]4)=[CH:42][CH:43]=3)=[N:26][C:25]=12)=[O:20]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 687534852-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridineHCID 867030466-(2,6-Difluorophenyl)-5-(4-formylphenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester

Product 1

HCID 178498893HCID 178498893, compound

Reagents, catalysts & solvents 3

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

Procedure

394.5 mg 2-(5-Azetidine-3-yl-[1,2,4]triazole-3-yl)-6-methylpyridine×2HCl (60% pure) are dissolved in 7 mL NMP. After addition of 0.3 mL triethylamine the reaction mixture is stirred for one hour. 350 mg (0.89 mmol) 6-(2,6-Difluorophenyl)-5-(4-formylphenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester and 0.09 mL acetic acid are added. The reaction mixture is stirred overnight at room temperature. 207.4 mg (0.98 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) 191.9 mg (34.6%) of the desired product are obtained.

Workup

  1. stirringThe reaction mixture is stirred overnight 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-6d9a03de2d254a198a5a223e931b100a
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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