Acetic Acid → HCID 178432368, compound

HRID 1851255Notes

Reaction equation

HRID 1851255 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]2[NH:10][N:9]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[N:7]=2)[CH2:3]1.[CH3:17][C:18]1[N:40]=[C:21]2[N:22]=[C:23]([C:32]3[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=3)[C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:25][N:20]2[N:19]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(N(CC)CC)C.CN(C=O)C>[CH3:17][C:18]1[N:40]=[C:21]2[N:22]=[C:23]([C:32]3[CH:33]=[CH:34][C:35]([CH2:36][N:2]4[CH2:5][CH:4]([C:6]5[N:7]=[C:8]([C:11]6[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=6)[NH:9][N:10]=5)[CH2:3]4)=[CH:38][CH:39]=3)[C:24]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:25][N:20]2[N:19]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydride2×HCID 687522832-(5-Azetidine-3-yl-[1,2,4]triazol-3-yl)-pyridine hydrochloride saltHCID 866306814-(2-Methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Product 1

HCID 178432368HCID 178432368, compoundYield 27.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

77 mg (0.38 mmol) 2-(5-azetidine-3-yl-[1,2,4]triazol-3-yl)-pyridine hydrochloride salt was dissolved in 6 mL methanol and 0.1 mL triethylamine. After addition of 100 mg (0.31 mmol) 4-(2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde dissolved in 6 mL DMF, 0.06 mL acetic acid and 131 mg (0.76 mmol) NaBH(OAc)3 the reaction mixture was stirred at room temperature. Three additional portions of 2 equivalents NaBH(OAc)3 each were added after 2, 4 and 6 hours. The solvent was removed by evaporation and the residue was purified by chromatography on silica gel (dichloromethane/methanol) to yield 42 mg of the desired product.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-bedc515aa5674432a3975fb2a9e1b2ab
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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