Nicotinic Acid → HCID 25181485, compound

HRID 2382787Notes

Reaction equation

HRID 2382787 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[O:10]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]3[N:21]=[C:22]([NH2:24])[N:23]=[C:19]3[CH:18]=[CH:17][CH:16]=2)=[CH:11]1.CC(C)([O-])C.[Na+].CCOCC>C1COCC1>[O:10]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]3[N:21]=[C:22]([NH:24][C:1](=[O:9])[C:2]4[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=4)[N:23]=[C:19]3[CH:18]=[CH:17][CH:16]=2)=[CH:11]1

Participants

6

Reactant 4

HCID 938Nicotinic AcidHCID 3283Diethyl EtherHCID 23676156Sodium t-butoxideHCID 252159385-(Furan-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 25181485HCID 25181485, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of nicotinic acid (74 mg, 0.6 mmol, 1.2 eq.) and 1,1-carbonyldiimidazole (122 mg, 0.75 mmol, 1.5 eq.) in dry THF (1 mL) was stirred for 45 min. at rt. In parallel, a solution of 5-(3-furyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine ((A2), 100 mg; 0.50 mmol; 1.0 eq.) and sodium tert-butoxide (96 mg, 1.0 mmol, 2.0 eq.) in dry THF (2 mL) was stirred for 45 min. at rt. The two solutions were then combined and the reaction mixture was stirred overnight at rt. Et2O was then added and the precipitate obtained was filtered, washed with Et2O, THF, a 5N solution of NaOH and water. It was resuspended in an acidic aqueous solution (pH 1) and filtered to give the title compound as a white powder (52.4 mg, 31%). HPLC, Rt: 1.98 min. (purity 95.1%). LC/MS, M+(ESI): 306.1, M−(ESI): 304.1.

Workup

  1. customthe precipitate obtained
  2. filtrationwas filtered
  3. washwashed with Et2O, THF
  4. filtrationfiltered

Sources & evidence

ORD record
ord-0b33088555854c4596c530834b73e1b2
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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