3,5-Dimethyl-4-Isoxazolecarbaldehyde → 5-[4-(3,5-Dimethyl-isoxazol-4-ylmethyl)-piperazin-1-yl]-2-(3-fluoro-phenyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

HRID 1181297Notes

Reaction equation

HRID 1181297 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:23]=[C:11]3[N:12]=[C:13]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[N:14]=[C:15]([NH2:16])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:24][C:25]1[C:29]([CH:30]=O)=[C:28]([CH3:32])[O:27][N:26]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH3:24][C:25]1[C:29]([CH2:30][N:20]2[CH2:19][CH2:18][N:17]([C:13]3[N:14]=[C:15]([NH2:16])[N:10]4[N:9]=[C:8]([C:4]5[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=5)[N:23]=[C:11]4[N:12]=3)[CH2:22][CH2:21]2)=[C:28]([CH3:32])[O:27][N:26]=1

Participants

6

Reactant 3

HCID 2895763,5-Dimethyl-4-IsoxazolecarbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 694310402-(3-Fluoro-phenyl)-5-piperazin-1-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

Product 1

HCID 111777095-[4-(3,5-Dimethyl-isoxazol-4-ylmethyl)-piperazin-1-yl]-2-(3-fluoro-phenyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2-(3Fluoro-phenyl)-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 3,5-dimethyl-isoxazole-4-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 6.9-7.25 (m, 3 H), 3.8 (br s, 2H), 2.2-3.2 (m, 8H), 1.6 (br s, 6H). MS: m/z: 424 [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-6c1d1786a26142b2835e6ad647e234fa
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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