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

HRID 85102
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 85102
[Cl:1][C:2]1[C:7]([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:6][CH:5]=[CH:4][N:3]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>CS(C)=O.O>[Cl:1][C:2]1[C:7]([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:6][CH:5]=[CH:4][N:3]=1.[O:28]1[CH2:29][CH2:30][N:25]([C:2]2[C:7]([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:6][CH:5]=[CH:4][N:3]=2)[CH2:26][CH2:27]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 8083MorpholineHCID 866537882-(2-Chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide

Produkt 2

HCID 446006392-(2-morpholinopyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamideAusbeute 120,7 %HCID 866537882-(2-Chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679
Dimethyl Sulfoxide
Lösungsmittel
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

2-(2-Chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide 9 was prepared according to the general procedure outlined above using the appropriate aldehyde component. A mixture containing this material, namely 2-(2-chloropyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide (9; 19 mg, 0.053 mmol) and morpholine (48; 46 mg, 0.53 mmol) in DMSO (1.2 mL) were 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-(2-morpholinopyridin-3-yl)-N-(thiazol-2-yl)-1H-benzo[d]imidazole-4-carboxamide (Compound 250) as a white solid (13 mg, 60%). MS (ESI) calcd for C20H18N6O2S (m/z): 406.12; found: 407 [M+H].

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe precipitated solids were collected by filtration
  3. customdried
  4. dissolutionThe solids were redissolved in EtOAc
  5. additionenough petroleum ether was added
  6. customto precipitate the product out again
  7. filtrationThe solids were collected by filtration
  8. washwashed with MeOH
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4377b2a8f7b341b4be9cfa3c6fbf1cff
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846947B2

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