M-Cresol → HCID 42597470, compound

HRID 1472797Notes

Reaction equation

Br[C:2]1[N:7]2[N:8]=[C:9]([NH2:11])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:19].C(=O)([O-])[O-].[K+].[K+].[CH3:26][C:27](N(C)C)=[O:28].O1CCO[CH2:34][CH2:33]1>>[C:13]1([CH3:19])[CH:14]=[CH:15][CH:16]=[C:17]([O:18][C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:27]([CH:26]4[CH2:34][CH2:33]4)=[O:28])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH:12]=1

Participants

Reactant 5

HCID 342M-Cresol

HCID 11430Potassium Carbonate

HCID 312751,4-Dioxane

HCID 31374Dimethylacetamide

HCID 252159395-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 42597470HCID 42597470, compound

Conditions

Temperature: 180 °C

Procedure

5-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (0.05 g, 0.178 mmol) and m-cresol (0.096 g, 0.889 mmol) were dissolved in dioxane (1 mL). Potassium carbonate (0.123 g, 0.889 mmol) and a couple of drop of dimethylacetamide were added and the mixture was heated to 180° C. for 30 mins in the microwave. The crude product was filtered and purified by preparatory HPLC. LCMS method: 2, RT: 3.63 min, MI: 309.

Workup

filtrationThe crude product was filtered
custompurified by preparatory HPLC

Sources & evidence

ORD record: ord-9157a122001845dd9cddb8559eebc9bd
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012633B2

Reaction notes

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