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Water → HCID 178419950, Verbindung

HRID 1846783
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1846783
[H-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]1.[O:20]1[CH2:25][CH:24]=[C:23]([C:26]2[C:27](F)=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:22][CH2:21]1.O>CN1C(=O)CCC1>[O:20]1[CH:21]=[CH:22][CH:23]([C:26]2[C:27]([O:19][C@H:16]3[CH2:15][CH2:14][C@H:13]([NH:12][C:4]4[S:3][C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=5[N:5]=4)[CH2:18][CH2:17]3)=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:24][CH2:25]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 593267823-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridineHCID 178521592HCID 178521592, Verbindung

Produkt 1

HCID 178419950HCID 178419950, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Sodium hydride (0.054 g, 1.3 mmol, 60% dispersion in mineral oil) was added to a mixture of trans-4-(benzo[d]thiazol-2-ylamino)cyclohexanol (0.17 g, 0.67 mmol) in NMP (1.5 mL) in a microwave tube. The tube was sealed and placed under an argon atmosphere. The mixture was stirred at RT for 45 min before 3-(3,6-dihydro-2H-pyran-4-yl)-2-fluoropyridine, as prepared in preparation 1a, step 1, (0.10 g, 0.56 mmol) was added via syringe. The reaction mixture was warmed to 120° C. and stirred for 1 h. Water was added, and the aqueous mixture was extracted with EtOAc (2×). The organic extracts were combined, washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified via silica gel chromatography to give both N-(trans-4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)cyclohexyl)benzo[c/]thiazol-2-amine and N-(trans-4-(3-(3,4-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)cyclohexyl)benzo[d]thiazol-2-amine as white solids. [M+1] 408.1 each. IC50 (uM): 0.007281 (Example 3b) and 0.9154 (Example 3c).

Aufarbeitung

  1. customThe tube was sealed
  2. additionwas added via syringe
  3. extractionthe aqueous mixture was extracted with EtOAc (2×)
  4. washwashed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product was purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-744832b2aa2f4927a885b6b1b9fe4956
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08952037B2

Notizen zur Reaktion

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