Cesium carbonate → HCID 67773599, compound

HRID 1802316Notes

Reaction equation

Br[C:2]1[N:27]=[C:5]2[CH:6]=[C:7]([NH:10][C:11]([C:13]3[N:17]([CH3:18])[N:16]=[CH:15][C:14]=3[C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:20])=[O:12])[CH:8]=[CH:9][N:4]2[N:3]=1.[NH:28]1[CH2:32][CH2:31][CH2:30][C:29]1=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[O:33]=[C:29]1[CH2:30][CH2:31][CH2:32][N:28]1[C:2]1[N:27]=[C:5]2[CH:6]=[C:7]([NH:10][C:11]([C:13]3[N:17]([CH3:18])[N:16]=[CH:15][C:14]=3[C:19]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:20])=[O:12])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To an argon purged solution of N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-4-(morpholine-4-carbonyl)-1H-pyrazole-5-carboxamide (40 mg, 92.1 μmol) in dioxane (1.84 ml) were added pyrrolidin-2-one (8.47 μl, 111 μmol), cesium carbonate (42.0 mg, 129 μmol), tris(dibenzylideneacetone)dipalladium(0) (1.69 mg, 1.84 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (2.13 mg, 3.68 μmol). The resulting mixture was heated to 100° C. and stirred overnight under argon atmosphere. The crude material was applied on SiO2 and purified by flash chromatography over a 5 g SiO2 column using heptane/ethyl acetate 10-100% to ethyl acetate/methanol 2% as eluent to give 2-methyl-4-(morpholine-4-carbonyl)-2H-pyrazole-3-carboxylic acid [2-(2-oxo-pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide (23 mg, 57%) as light yellow solid. mp: 269.9, MS: m/z=439.1 (M+H+).

Workup

custompurified by flash chromatography over a 5 g SiO2 column

Sources & evidence

ORD record: ord-704eca51ad47439c941da1ef8972250c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

Loading…