Water → [4-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-thianthren-1-yloxy]-acetic acid methyl ester

HRID 33799Notes

Reaction equation

[OH:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([C:16]2[O:17][C:18]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:19][C:20](=[O:22])[CH:21]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:35][O:36][C:37](=[O:40])[CH2:38]Br.O>CN(C)C=O>[CH3:35][O:36][C:37](=[O:40])[CH2:38][O:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[S:7][C:6]=2[C:5]([C:16]2[O:17][C:18]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:19][C:20](=[O:22])[CH:21]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-(4-Hydroxy-thianthren-1-yl)-6-morpholin-4-yl-pyran-4-one (130) (1.20 g, 2.91 mmol) in dimethylformamide (10 ml), under and inert atmosphere, was added powdered potassium carbonate (1.21 g, 8.75 mmol) and methylbromoacetate (0.55 ml, 5.82 mmol). The temperature of the reaction was raised to 60° C. for 48 hours and then cooled to room temperature before the addition of water (20 mL). The mixture was then extracted using ethyl acetate (3×30 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo to give the title compound as an off white solid (1.40 g, 99%) that was suitably clan and required no further purification. m/z (LC-MS, ESP): RT=4.48 min, (M++1)=484

Workup

extractionThe mixture was then extracted
dry with materialThe combined organics were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a98757de6faa4031934c2f85cda29302
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429660B2

Reaction notes

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