Potassium Carbonate → N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]thiophene-2-carboxamide

HRID 715764

반응식

HRID 715764 반응식
Br[C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]3[CH:17]=[CH:18][N:19]=[C:13]3[CH:12]=2)=[O:8])=[CH:4][CH:3]=1.[CH:20]([C@@H:23]1[CH2:27][O:26][C:25](=[O:28])[NH:24]1)([CH3:22])[CH3:21].CN(C)CCN.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Cu]I>[N:19]1[CH:18]=[CH:17][N:14]2[CH:15]=[CH:16][C:11]([CH2:10][NH:9][C:7]([C:5]3[S:6][C:2]([N:24]4[C@H:23]([CH:20]([CH3:22])[CH3:21])[CH2:27][O:26][C:25]4=[O:28])=[CH:3][CH:4]=3)=[O:8])=[CH:12][C:13]=12

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 641505(4R)-4-(Propan-2-yl)-1,3-oxazolidin-2-oneHCID 867019355-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide

생성물 1

HCID 86701938N-(imidazo[1,2-a]pyridin-7-ylmethyl)-5-[(4R)-2-oxo-4-(propan-2-yl)-1,3-oxazolidin-3-yl]thiophene-2-carboxamide

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

실험 절차

A solution of 5-bromo-N-(imidazo[1,2-a]pyridin-7-ylmethyl)thiophene-2-carboxamide (84 mg, 0.25 mmol), (R)-4-isopropyloxazolidin-2-one (32 mg, 0.25 mmol), N,N-dimethylethane-1,2-diamine (2 mg, 0.025 mmol), copper(I) iodide (5 mg, 0.025 mmol) and potassium carbonate (121 mg, 0.88 mmol) in dioxane (1 ml) was stirred at 110° C. overnight. Concentration and reverse phase chromatography provided the title compound. 1H NMR (400 MHz, methanol-d4) δ ppm 9.13 (t, J=5.3 Hz, 1H), 8.74 (d, J=5.5 Hz, 1H), 8.17 (s, 1H), 7.99 (s, 1H), 7.79 (s, 1H), 7.62 (d, J=4.1 Hz, 1H), 7.47 (d, J=7.0 Hz, 1H), 6.77 (d, J=4.2 Hz, 1H), 4.72 (s, 2H), 4.61-4.42 (m, 3H), 2.46 (ddd, J=10.2, 6.9, 3.5 Hz, 1H), 1.00 (d, J=7.0 Hz, 3H), 0.85 (d, J=6.8 Hz, 3H); (APCI(+)) m/e 385 (M+H)+.

후처리

  1. concentrationConcentration

출처 및 근거

ORD 기록
ord-d09b01bd17a84e9f9ff897904aa22fbc
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187472B2

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