2-Pyridinecarboxaldehyde → 2-Furan-2-yl-5-(4-pyridin-2-ylmethyl-piperazin-1-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

HRID 1181286Notes

Reaction equation

HRID 1181286 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:21]=[C:9]2[N:10]=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH:28]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:21]=[C:9]2[N:10]=[C:11]([N:15]3[CH2:20][CH2:19][N:18]([CH2:28][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=4)[CH2:17][CH2:16]3)[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=1

Participants

6

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 114490312-Furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

Product 1

HCID 114743762-Furan-2-yl-5-(4-pyridin-2-ylmethyl-piperazin-1-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2-Furan-2-yl-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.15 mmol) was dissolved in 4 mL of CH2Cl2 along with 2 eq. of pyridine-2-carbaldehyde and 25 mL of glacial acetic acid. The reaction mixture was stirred at room temperature for 30 minutes and sodium triacetoxyborohydride (4 eq.) was added in a single portion. The resulting reaction mixture was then stirred at room temperature for 18 hours. It was then concentrated under a stream of N2 and purified by preparative HPLC using a mixture of aqueous CH3CN that has been buffered with 0.1% TFA. 1H NMR (DMSO-d6) δ 8.52 (d, J=6.0 Hz, 1H), 7.64-7.60 (m, 1H), 7.50-7.19 (m, 4H), 6.84 (dd, J=3.6 Hz, 1.0 Hz, 1H), 4.09-4.06 (m, 4H), 3.89 (br s, 2H), 2.51-2.41 (m, 4H) ppm. MS: m/z: 378 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas then stirred at room temperature for 18 hours
  3. concentrationIt was then concentrated under a stream of N2
  4. custompurified by preparative HPLC
  5. additiona mixture of aqueous CH3CN that

Sources & evidence

ORD record
ord-99e159a80ccb4638a2f2de85d151eb8e
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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