Cesium carbonate → N-(5-((1S,3S)-3-(5-amino-1,3,4-thiadiazol-2-yl)cyclohexyl)-1,3,4-thiadiazol-2-yl)-2-(pyridin-2-yl)acetamide

HRID 572944Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10]C)=O.[C@H:12]1([C:24]2[S:28][C:27]([NH2:29])=[N:26][N:25]=2)[CH2:17][CH2:16][CH2:15][C@H:14]([C:18]2[S:22][C:21]([NH2:23])=[N:20][N:19]=2)[CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[NH2:29][C:27]1[S:28][C:24]([C@H:12]2[CH2:17][CH2:16][CH2:15][C@H:14]([C:18]3[S:22][C:21]([NH:23][C:8](=[O:10])[CH2:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)=[N:20][N:19]=3)[CH2:13]2)=[N:25][N:26]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of methyl 2-(pyridin-2-yl)acetate (107.0 mg, 0.71 mmol), 5,5′-((1S,3S)-cyclohexane-1,3-diyl)bis(1,3,4-thiadiazol-2-amine) (200 mg, 0.71 mmol), cesium carbonate (762.7 mg, 1.42 mmol) in DMF (6 mL) was heated to 130° C. under nitrogen atmosphere and microwave for 45 min. The mixture was evaporated in vacuum to dryness. The residue was purified by a standard method to afford desired compound.

Workup

customThe mixture was evaporated in vacuum to dryness
customThe residue was purified by a standard method

Sources & evidence

ORD record: ord-f8a72d3fb58d40399fa8bf6d60275429
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029531B2

Reaction notes

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