Diisopropylethylamine → N-Cyclopropyl-N-[1-(5-ethyl-pyrimidin-2-yl)-piperidin-4-yl]-4-oxazol-5-yl-benzamide

HRID 68819Notes

Reaction equation

Cl.[CH:2]1([N:5]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:6](=[O:18])[C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:17][CH:16]=[N:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:4][CH2:3]1.C(N(C(C)C)C(C)C)C.Cl[C:35]1[N:40]=[CH:39][C:38]([CH2:41][CH3:42])=[CH:37][N:36]=1>CN(C)C=O.O1CCOCC1>[CH:2]1([N:5]([CH:19]2[CH2:24][CH2:23][N:22]([C:35]3[N:40]=[CH:39][C:38]([CH2:41][CH3:42])=[CH:37][N:36]=3)[CH2:21][CH2:20]2)[C:6](=[O:18])[C:7]2[CH:8]=[CH:9][C:10]([C:13]3[O:17][CH:16]=[N:15][CH:14]=3)=[CH:11][CH:12]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-cyclopropyl-4-oxazol-5-yl-N-piperidin-4-yl-benzamide hydrogen chloride salt (52 mg), ethyldiisopropylamine (59 mg), and 2-chloro-5-ethylpyrimidine (21 mg) in N,N-dimethylformamide (1.0 mL) and 1,4-dioxane (1.5 mL) is stirred over night at 120° C. After cooling to room temperature, the solvents are evaporated and the residue is purified by HPLC (H2O/MeOH/TFA) to give the title compound. LC (method 9): tR=1.74 min; Mass spectrum (ESI+): m/z=418 [M+H]+.

Workup

temperatureAfter cooling to room temperature
customthe solvents are evaporated
customthe residue is purified by HPLC (H2O/MeOH/TFA)

Sources & evidence

ORD record: ord-bf4170711eb04fa2b341ec10d300b61a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822471B2

Reaction notes

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