Methyl iodide → HCID 69670981, compound

HRID 1497572Notes

Reaction equation

[C:1]([C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[N:21][N:22]=3)[CH:19]=2)=[CH:10][CH:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:34]>C1COCC1>[CH3:34][N:7]([C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[O:6])[C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[N:21][N:22]=3)[CH:19]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 6-(4-t-butylcarbonylaminophenyl)-3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine (120 mg, 0.29 mmol) in dry THF (20 mL) cooled at 0° C. was added NaH (12 mg, 0.32 mmol), and it was stirred for 2 h. To the mixture was added iodomethane (164 mg, 1.5 mmol) in THF (8 mL) dropwise, and the mixture was stirred at room temperature overnight. The reaction mixture was quenched with saturated NH4Cl (20 mL) and extracted with ethyl acetate (100 mL×3). The combined organic phase was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue was purified by preparative TLC to give the title compound (38 mg, 31% yield) as yellow solids. MS: m/z 431.3 [M+H+].

Workup

stirringthe mixture was stirred at room temperature overnight
customThe reaction mixture was quenched with saturated NH4Cl (20 mL)
extractionextracted with ethyl acetate (100 mL×3)
dry with materialThe combined organic phase was dried over anhydrous Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated
customthe residue was purified by preparative TLC

Sources & evidence

ORD record: ord-6228bc61c5f14a2cb8d1b597fc6faa29
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199983B2

Reaction notes

Loading…