1,10-Phenanthroline → N-[7-methoxy-4-(tetrahydro-pyran-4-yl)-thiazolo[5,4-c]pyridin-2-yl]-benzamide

HRID 917475Notes

Reaction equation

[C:1]([NH:9][C:10]([NH:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][N:16]=[C:15]([CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:14]=1I)=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[CH3:20][O:19][C:18]1[C:13]2[N:12]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:11][C:14]=2[C:15]([CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[N:16][CH:17]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A stirred suspension of 760 mg (1.53 mmol) 1-benzoyl-3-[3-iodo-5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-yl]-thiourea, 29 mg (0.15 mmol) copper(I) iodide, 55 mg (0.31 mmol) 1,10-phenanthroline and 1.00 g (3.06 mmol) cesium carbonate in 4 ml toluene was heated at 130° C. for 10 min in a microwave oven. The resulting mixture was then cooled to room temperature and concentrated in vacuo. The residue was resuspended in methanol, the mixture filtered, and the filtrate concentrated in vacuo. Flash chromatography (ethyl acetate/heptane) afforded 314 mg (56%) N-[7-methoxy-4-(tetrahydro-pyran-4-yl)-thiazolo[5,4-c]pyridin-2-yl]-benzamide as a white solid. ES-MS m/e (%): 370 (M+H+, 100).

Workup

temperatureThe resulting mixture was then cooled to room temperature
concentrationconcentrated in vacuo
filtrationthe mixture filtered
concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record: ord-03f8457d5f004f0c9f71eff95168d66a
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273865B2

Reaction notes

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