Trimethylaluminum → 4-(azetidine-1-carbonyl)-1-methyl-N-(8-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-5-carboxamide

HRID 1802157Notes

Reaction equation

[CH3:1][C:2]1[C:3]2[N:4]([N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].C[Al](C)C.[N:22]1([C:26]([C:28]2[CH:29]=[N:30][N:31]([CH3:38])[C:32]=2[C:33](OCC)=[O:34])=[O:27])[CH2:25][CH2:24][CH2:23]1>O1CCOCC1>[N:22]1([C:26]([C:28]2[CH:29]=[N:30][N:31]([CH3:38])[C:32]=2[C:33]([NH:8][C:7]2[CH:6]=[CH:5][N:4]3[N:9]=[C:10]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:11]=[C:3]3[C:2]=2[CH3:1])=[O:34])=[O:27])[CH2:23][CH2:24][CH2:25]1

Participants

Conditions

Temperature: 25 °C

Procedure

To an argon purged solution of 8-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-amine (60 mg, 268 μmol) in dioxane (5 ml) is added trimethylaluminum (2M solution in toluene, 401 μl, 803 μmol). The resulting mixture is stirred for 1 hour at 25° C., then ethyl 4-(azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxylate (63.5 mg, 268 μmol) is added, the mixture is heated to 100° C. and stirred for 72 hours. The crude material is loaded on silica and purified by flash chromatography on a 20 g silica column using heptane/ethyl acetate 50-100% as eluent affording 4-(azetidine-1-carbonyl)-1-methyl-N-(8-methyl-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1H-pyrazole-5-carboxamide (77 mg, 69.3%) as a white solid. mp.: 243-5° C. MS: m/z=416.2 (M+H+).

Workup

temperaturethe mixture is heated to 100° C.
stirringstirred for 72 hours
custompurified by flash chromatography on a 20 g silica column

Sources & evidence

ORD record: ord-a19fbea4f1274fb7b991e66e00cebea3
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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