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Diethyl Ether → 4-(Pyrrolidin-1-yl)piperidine-1-carboxylic acid {4-[3-fluoro-4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide

HRID 492793
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 492793
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]3[CH2:21][CH2:20][CH:19]([N:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=[CH:4][C:3]=1[F:29].[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[C:45]1([CH2:51][C:52]([N:54]=[C:55]=[S:56])=[O:53])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(OCC)C>C(O)C.C1(C)C=CC=CC=1.CCCCCC>[F:29][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][C:2]=1[NH:1][C:55]([NH:54][C:52](=[O:53])[CH2:51][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[S:56])[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][CH:19]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH2:18][CH2:17]2)=[O:15])[CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 3283Diethyl EtherHCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 12454157Phenylacetyl isothiocyanateHCID 576775624-(Pyrrolidin-1-yl)piperidine-1-carboxylic acid [4-(4-amino-3-fluorophenoxy)pyridin-2-yl]amide

Produkt 1

HCID 576773594-(Pyrrolidin-1-yl)piperidine-1-carboxylic acid {4-[3-fluoro-4-(3-phenylacetylthioureido)phenoxy]pyridin-2-yl}amide
Ausbeute 18 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

4-(Pyrrolidin-1-yl)piperidine-1-carboxylic acid [4-(4-amino-3-fluorophenoxy)pyridin-2-yl]amide was dissolved in ethanol (3.0 ml), and then (S)-(+)-10-camphorsulfonic acid (75.5 mg) was added thereto, followed by stirring at room temperature for 15 min. A solution of phenylacetyl isothiocyanate (45.5 mg) in toluene (3.0 ml) was added thereto, followed by stirring at room temperature for 2.5 hrs. The reaction mixture was partitioned between ethyl acetate (50 ml) and a saturated aqueous solution of sodium hydrogencarbonate (30 ml). The organic layer was washed with brine (30 ml×3), and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (FUJI Silysia NH, eluent; heptane:ethyl acetate=1:2, ethyl acetate, then ethyl acetate). Fractions containing the target compound were concentrated to give a solid, to which diethyl ether (3 ml) and hexane (3 ml) in this order were then added to suspend. The solid was filtered off, washed with diethyl ether (1 ml), and dried under aeration to provide the titled compound (17.8 mg, 18%) as colorless powder.

Aufarbeitung

  1. stirringby stirring at room temperature for 2.5 hrs
  2. customThe reaction mixture was partitioned between ethyl acetate (50 ml)
  3. washThe organic layer was washed with brine (30 ml×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customto give a residue, which
  7. customwas then purified by silica gel column chromatography (FUJI Silysia NH, eluent
  8. additionFractions containing the target compound
  9. concentrationwere concentrated
  10. customto give a solid
  11. filtrationThe solid was filtered off
  12. washwashed with diethyl ether (1 ml)
  13. customdried under aeration

Quellen und Nachweise

ORD-Eintrag
ord-df71f61b6a3a4969a545c8dcb414d5f3
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07531532B2

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