Triethylamine → HCID 178498895, compound

HRID 1851293Notes

Reaction equation

HRID 1851293 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.C(N(CC)CC)C.[CH3:26][O:27][C:28]([C:30]1[CH:31]=[N:32][N:33]2[CH:38]=[C:37]([C:39]3[C:44]([F:45])=[CH:43][CH:42]=[CH:41][C:40]=3[F:46])[C:36]([C:47]3[CH:52]=[CH:51][C:50]([CH:53]=O)=[CH:49][CH:48]=3)=[N:35][C:34]=12)=[O:29].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN1C(=O)CCC1.C(O)(=O)C>[CH3:26][O:27][C:28]([C:30]1[CH:31]=[N:32][N:33]2[CH:38]=[C:37]([C:39]3[C:40]([F:46])=[CH:41][CH:42]=[CH:43][C:44]=3[F:45])[C:36]([C:47]3[CH:48]=[CH:49][C:50]([CH2:53][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:51][CH:52]=3)=[N:35][C:34]=12)=[O:29]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 867030466-(2,6-Difluorophenyl)-5-(4-formylphenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl esterHCID 178424635HCID 178424635, compound

Product 1

HCID 178498895HCID 178498895, compound

Reagents, catalysts & solvents 2

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

Procedure

402 mg (1.27 mmol) 2-Methyl-6-(5-piperidine-4-yl-2H-[1,2,4]triazole-3-yl)-pyridine×2HCl are dissolved in 10 mL NMP. After addition of 0.43 mL triethylamine the reaction mixture is stirred for one hour. 500 mg (1.27 mmol) 6-(2,6-Difluorophenyl)-5-(4-formylphenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid methyl ester and 0.13 mL acetic acid are added. The reaction mixture is stirred over night at room temperature. 296.3 mg (1.40 mmol) NaBH(OAc)3, are added in portions and the reaction mixture is stirred at room temperature for 5 hours. After treatment of the reaction mixture with saturated NaHCO3 the precipitate is filtered off, washed with water and dried. After chromatography of the precipitate on silica gel (dichloromethane/methanol) 368.6 mg (44.4%) 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. filtrationAfter treatment of the reaction mixture with saturated NaHCO3 the precipitate is filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-36c614f02c764db5ae8ffa5087e6ff1e
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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