Thiophenol → HCID 59589798, compound

HRID 1472798Notes

Reaction equation

[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:11]1[N:16]2[N:17]=[C:18]([NH:20][C:21]([CH:23]3[CH2:25][CH2:24]3)=[O:22])[N:19]=[C:15]2[CH:14]=[CH:13][CH:12]=1>>[C:3]1([S:9][C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:21]([CH:23]4[CH2:24][CH2:25]4)=[O:22])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 7969Thiophenol

HCID 24758Sodium hydride

HCID 59179473N-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 59589798HCID 59589798, compound

Conditions

Temperature: 160 °C

Procedure

A microwave tube was charged with sodium hydride (0.036 g, 0.889 mmol) in anhydrous well-degassed dioxane (1 mL). Thiophenol (0.091 mL, 0.889 mmol) was added dropwise and the mixture allowed to stir for 5 min. Cyclopropanecarboxylic acid (5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-amide (0.05 g, 0.178 mmol) was added and the mixture was heated to 160° C. for 20 min in a microwave. The crude product was purified by preparatory HPLC. LCMS method: 2, RT: 4.32 min, MI: 311 [M+1]. NMR (1H, DMSO, 300 MHz): 11.17 (s, 1H), 7.70 (m, 2H), 7.57 (m, 3H), 7.49 (d, 2H), 6.28 (t, 1H), 2.03 (brs, 1H), 0.83 (d, 4H)

Workup

customin anhydrous well-degassed dioxane (1 mL)
customThe crude product was purified by preparatory HPLC

Sources & evidence

ORD record: ord-be3ae8430e9041048d5b79952ec6ebb2
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012633B2

Reaction notes

Loading…