Isopropanol → N-Cyclopropyl-N-[1-(3-isopropoxy-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

HRID 68837Notes

Reaction equation

Cl[C:2]1[N:6]=[C:5]([N:7]2[CH2:12][CH2:11][CH:10]([N:13]([CH:27]3[CH2:29][CH2:28]3)[C:14](=[O:26])[C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][CH:24]=[N:23][CH:22]=4)=[CH:17][CH:16]=3)[CH2:9][CH2:8]2)[S:4][N:3]=1.[CH:30]([OH:33])([CH3:32])[CH3:31].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[CH:27]1([N:13]([CH:10]2[CH2:11][CH2:12][N:7]([C:5]3[S:4][N:3]=[C:2]([O:33][CH:30]([CH3:32])[CH3:31])[N:6]=3)[CH2:8][CH2:9]2)[C:14](=[O:26])[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[O:25][CH:24]=[N:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:29][CH2:28]1

Participants

Conditions

Temperature: 125 °C

Procedure

A mixture of N-[1-(3-chloro-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-N-cyclopropyl-4-oxazol-5-yl-benzamide (43 mg), isopropanol (2.0 mL), and cesium carbonate (98 mg) in N-methyl-2-pyrrolidinon (2.0 mL) is stirred at 125° C. for three days. The mixture is separated by HPLC (MeOH/H2O/TFA) to give the title compound. LC (method 5): tR=2.14 min; Mass spectrum (ESI+): m/z=454 [M+H]+.

Workup

customThe mixture is separated by HPLC (MeOH/H2O/TFA)

Sources & evidence

ORD record: ord-c7cc8e98d6e94c7e9747bf249fa2d017
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822471B2

Reaction notes

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