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Ammonia → 5-[6-(aminomethyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

HRID 2391615
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2391615
CS(O[CH2:6][C:7]1[N:12]=[CH:11][C:10]2[N:13]([C:16]3[S:17][C:18]([C:34](=[O:36])[NH2:35])=[C:19]([O:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])[CH3:23])[CH:20]=3)[CH:14]=[N:15][C:9]=2[CH:8]=1)(=O)=O.[NH3:37]>CO>[NH2:37][CH2:6][C:7]1[N:12]=[CH:11][C:10]2[N:13]([C:16]3[S:17][C:18]([C:34]([NH2:35])=[O:36])=[C:19]([O:21][C@@H:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:31])[F:32])[CH3:23])[CH:20]=3)[CH:14]=[N:15][C:9]=2[CH:8]=1
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Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 86647106[3-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-3H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate

Produkt 1

HCID 687669945-[6-(aminomethyl)-3H-imidazo[4,5-c]pyridin-3-yl]-3-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 150 mg of crude [3-(5-carbamoyl-4-{(1R)-1-[2-(trifluoromethyl)phenyl]ethoxy}-2-thienyl)-3H-imidazo[4,5-c]pyridin-6-yl]methyl methanesulfonate (example 49, step 1) in 5 ml of a saturated solution of ammonia in methanol is stirred in a microwave vial at 80° C. for 1 h in the microwave cavity. The solvent is removed under reduced pressure. 20 ml of water and 20 ml dichloromethane is added to the residue, the organic phase is separated and the aqueous phase is extracted with 2×10 ml dichloromethane. The combined organic layers are dried over MgSO4, filtered and evaporated under reduced pressure. The resulting residue is purified by flash chromatography [silica gel, eluent: dichloromethane/methanol/7 N solution of ammonia in methanol, 9/1/0.3 (v/v/v)] to yield the title product.

Aufarbeitung

  1. customThe solvent is removed under reduced pressure
  2. addition20 ml of water and 20 ml dichloromethane is added to the residue
  3. customthe organic phase is separated
  4. extractionthe aqueous phase is extracted with 2×10 ml dichloromethane
  5. dry with materialThe combined organic layers are dried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe resulting residue is purified by flash chromatography [silica gel, eluent: dichloromethane/methanol/7 N solution of ammonia in methanol, 9/1/0.3 (v/v/v)]

Quellen und Nachweise

ORD-Eintrag
ord-8c1d458b8d1648348a74b2705c079b7b
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08273890B2

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