Sodium Acetate → 4-[5-Benzyl-3-(4-chloro-phenyl)-[1,2,4]triazol-1-yl]-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine

HRID 1797137

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([NH:8][C:9](=O)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=S)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].C(O)(=O)C.O1CCOCC1.[NH:35]([C:37]1[N:42]=[C:41]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[N:40]=[C:39]([NH2:49])[N:38]=1)[NH2:36]>O>[CH2:10]([C:9]1[N:35]([C:37]2[N:42]=[C:41]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=3)[N:40]=[C:39]([NH2:49])[N:38]=2)[N:36]=[C:6]([C:5]2[CH:18]=[CH:19][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:8]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of N-(4-chloro-thiobenzoyl)-2-phenyl-acetamide (0.536 g, 1.85 mmol) and sodium acetate (ca. 0.25 g) in 1:1 acetic acid/1,4-dioxane (30 mL) was added 4-hydrazino-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine (0.376 g, 1.85 mmol). The solution was heated to 90° C. and stirred for 15 hours. The reaction mixture was allowed to cool to room temperature, and water (100 mL) was added. The precipitate was removed by filtration, triturated with hot ethanol (300 mL), and dried to provide 0.489 g (60%) of the product as a white solid: 1H NMR (DMSO-d6) δ 8.78 (d, J=4.3 Hz, 1H), 8.32 (d, J=6.1 Hz, 2H), 8.22 (d, J=7.8 Hz, 1H), 8.06 (d, J=8.5 Hz, 2H), 7.96 (dt, J=1.5, 7.8 Hz, 1H), 7.62–7.57 (m, 3H), 7.36–7.26 (m, 2H), 7.24–7.22 (m, 2H), 7.19–7.16 (m, 1H), 4.90 (s, 2H) ppm.

Workup

temperatureto cool to room temperature
customThe precipitate was removed by filtration
customtriturated with hot ethanol (300 mL)
customdried

Sources & evidence

ORD record: ord-7460869d9e064d709ea3ccfafaf6d52b
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034031B2

Linked notes

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