Morpholine → 2-(6-morpholinopyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide

HRID 85101Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture containing 2-(6-chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide (7; 20 mg, 0.056 mmol) and morpholine (48; 49 mg, 0.56 mmol) in DMSO (1.5 mL) was stirred at 140° C. in a microwave reactor for 25 min. The reaction mixture was cooled to room temperature and diluted with water. The precipitated solids were collected by filtration and dried. The solids were redissolved in EtOAc and enough petroleum ether was added to precipitate the product out again. The solids were collected by filtration, washed with MeOH and dried to afford 2-(6-morpholinopyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide (Compound 247) as a pale yellow solid (13 mg, 57%). MS (ESI) calcd for C20H18N6O2S: 406.12; found: 407 [M+H].

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe precipitated solids were collected by filtration
customdried
dissolutionThe solids were redissolved in EtOAc
additionenough petroleum ether was added
customto precipitate the product out again
filtrationThe solids were collected by filtration
washwashed with MeOH
customdried

Sources & evidence

ORD record: ord-231e98344e4046c4a087d32548f35da9
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846947B2

Reaction notes

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