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

HRID 68836Notes

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]([NH2:33])([CH3:32])[CH3:31]>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]([NH: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: 120 °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) and isopropylamine (0.50 mL) in N-methyl-2-pyrrolidinon (1.50 mL) is stirred at 120° C. for two days. The mixture is concentrated in vacuo and the residue is purified by HPLC on reversed phase (MeOH/H2O/NH4OH). LC (method 5): tR=1.95 min; Mass spectrum (ESI+): m/z=453 [M+H]+.

Workup

concentrationThe mixture is concentrated in vacuo
customthe residue is purified by HPLC on reversed phase (MeOH/H2O/NH4OH)

Sources & evidence

ORD record: ord-33226bda70214009b0ca51bb18ba5dcb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822471B2

Reaction notes

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