HCID 71292891, compound → HCID 71292807, compound

HRID 1404208Notes

Reaction equation

[C:1]1([CH3:25])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]3[S:19][C:20]([C:23]#[N:24])=[CH:21][N:22]=3)[CH:13]=2)[O:8]1>O1CCCC1.[Ni]>[C:1]1([CH3:25])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]3[S:19][C:20]([CH2:23][NH2:24])=[CH:21][N:22]=3)[CH:13]=2)[O:8]1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-(2-o-tolyl-chroman-6-yloxy)-thiazole-5-carbonitrile (2.3 g, 6.6 mmol) in tetrahydrofuran (100 ml) an aqueous suspension of Raney nickel (approximately 500 mg) was added and the resulting suspension was vigorously stirred under an hydrogen atmosphere (atmospheric pressure) for 1 h (TLC control) at 45° C. The suspension was filtered through a celite plug and the filter cake washed with ethyl acetate. The organic layer was dried over sodium sulfate and filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, ethyl acetate/methanol gradient). [2-(2-o-Tolyl-chroman-6-yloxy)-thiazol-5-ylmethyl]amine was obtained as pale yellow oil (834 mg, 36%).

Workup

additionwas added
filtrationThe suspension was filtered through a celite plug
washthe filter cake washed with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
customthe solvent was removed under reduced pressure
customThe crude product was purified by column chromatography (silica gel, ethyl acetate/methanol gradient)

Sources & evidence

ORD record: ord-e9b413d9adf04a2b8c1aa6ae18ac6b64
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912224B2

Reaction notes

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