Morpholine → HCID 86689191, compound

HRID 589769Notes

Reaction equation

HRID 589769 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:13][C:14]3[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=3)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:12])=[O:11])=[C:7]([CH3:25])[C:6]=2[CH:26]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[CH3:25][C:7]1[C:6]2[CH:26]=[C:2]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH:3]=[CH:4][C:5]=2[S:9][C:8]=1[S:10]([NH:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 66799887HCID 66799887, compound2×

Product 1

HCID 86689191HCID 86689191, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl 3-{[(5-bromo-3-methyl-1-benzothiophen-2-yl)sulfonyl]amino}benzoate (Intermediate 18) (23 mg, 0.05 mmol), morpholine (9 mg, 0.10 mmol), PdOAc2 (0.6 mg, 0.0025 mmol), 2-(di-tbutylphosphino)biphenyl (1 mg, 0.0035 mmol) and Cs2CO3 (66 mg, 0.25 mmol) in dioxane (200 μL) was heated at 110° C. for 20 h giving the intermediate ethyl 3-{[(3-methyl-5-morpholin-4-yl-1-benzothiophen-2-yl)sulfonyl]amino}benzoate. The intermediate ester was hydrolyzed using LiOH in aqueous THF (1 mL, 1:1 water/THF) giving the title compound. MS (ESI+) calcd mass for C20H20N2O5S2 432.081363, found 432.081153.

Sources & evidence

ORD record
ord-bf2d67589ed1494eb55fc83bfc8bb512
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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