Acetic Acid → HCID 136227343, compound

HRID 1506169Notes

Reaction equation

HRID 1506169 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[N:8]=[N:9][N:10]3[C:15]=2[C:14]2[CH:16]=[CH:17][NH:18][C:13]=2[N:12]=[CH:11]3)[CH2:3][CH2:2]1.[C:19](O)(=O)[CH3:20].[C:23]([BH3-])#[N:24].[Na+].[C:27](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:28].[Na+].[CH3:41]O>O1CCCC1>[N:24]1[CH:23]=[CH:28][CH:27]=[C:19]([CH2:20][N:1]2[CH2:2][CH2:3][CH:4]([C:7]3[N:8]=[N:9][N:10]4[C:15]=3[C:14]3[CH:16]=[CH:17][NH:18][C:13]=3[N:12]=[CH:11]4)[CH2:5][CH2:6]2)[CH:41]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 136341302HCID 136341302, compound

Product 1

HCID 136227343HCID 136227343, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(Piperidin-4-yl)-7H-pyrrolo[3,2-e][1,2,3]triazolo[1,5-c]pyrimidine (11.0 mg, 0.0450 mmol) in a mixture of methanol (1 mL) and tetrahydrofuran (1 mL) was stirred with 3-pyridinecarboxyaldehyde (5.0 μL, 0.054 mmol), acetic acid (33 μL) and sodium cyanoborohydride (4.3 mg, 0.068 mmol) at room temperature for one day. The reaction mixture was stirred with sodium triacetoxyborohydride (10.0 mg, 0.047 mmol) for another 2 hours. The resulting reaction mixture was purified by silica gel thin layer chromatography (methanol/chloroform=1/9 (v/v)) twice to give the title compound as a colorless solid (1.4 mg, yield 9.3%).

Workup

  1. customThe resulting reaction mixture
  2. customwas purified by silica gel thin layer chromatography (methanol/chloroform=1/9 (v/v)) twice

Sources & evidence

ORD record
ord-4873e5a802ca43f2b487ae0a4d1ccccf
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

Loading…