Cesium carbonate → 4-(7-chloro-2-(methylthio)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide

HRID 1922270Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[S:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:13].Cl[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]([NH:23][CH3:24])=[O:22])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.O>[Cl:1][C:2]1[C:10]2[S:9][C:8]([S:11][CH3:12])=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:13][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]([NH:23][CH3:24])=[O:22])[CH:16]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To the solution of 7-chloro-2-(methylthio)benzo[d]thiazol-6-ol (80 mg, 0.346 mmol, 1.0 eq) in 1 mL of NMP was added 4-chloro-N-methylpicolinamide (88 mg, 0.519 mmol, 1.5 eq) and cesium carbonate (281 mg, 0.865 mmol, 2.5 eq) at room temperature. The reaction mixture was stirred at 85° C. for >48 hours till ca. 75%-80% completion, thereafter the mixture was diluted with water (ca. 50 mL) and aqueous layer extracted with ethyl acetate (ca. 50 mL×3). Combined organic layers were dried over sodium sulfate, filtered and condensed under reduced pressure to give crude product which was purified on ISCO using gradient 0%-100% ethyl acetate-hexane mixture to give 64 mg of product in 50% yield. LC/MS (m/z) [366.0] (MH+)

Workup

extractionextracted with ethyl acetate (ca. 50 mL×3)
dry with materialCombined organic layers were dried over sodium sulfate
filtrationfiltered
customcondensed under reduced pressure
customto give crude product which
customwas purified on ISCO

Sources & evidence

ORD record: ord-bfb9f6ba2d5e40d887ef00249d8bb777
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173689B2

Reaction notes

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