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Sodium Bicarbonate → HCID 57387591, Verbindung

HRID 1800624
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1800624
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[N:11]=[C:10]2[S:12][C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])=[N:14][C:9]2=[CH:8][CH:7]=1.[Cl:24][C:25]1[C:33]([CH:34]2[CH2:36][CH2:35]2)=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=O.F[P-](F)(F)(F)(F)F.[N:44]1(OC(N(C)C)=[N+](C)C)[C:48]2N=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[Cl:24][C:25]1[C:33]([C:34]2([C:48]#[N:44])[CH2:36][CH2:35]2)=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([NH:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:4]([O:5][C:6]2[N:11]=[C:10]3[S:12][C:13]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])=[N:14][C:9]3=[CH:8][CH:7]=2)[CH:3]=1)=[O:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57387081HCID 57387081, VerbindungHCID 684193892-Chloro-3-cyclopropylbenzoic acid

Produkt 1

HCID 57387591HCID 57387591, VerbindungAusbeute 8.664,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of N-[5-(3-aminophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (120 mg, 3.68 μmol) produced in Example C111(v), 2-chloro-3-(1-cyclopropyl)benzoic acid (90 mg, 405 μmol) produced in Example C62(ii) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (154 mg, 405 μmol) in pyridine (3 mL) was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (15 mL), and the mixture was extracted with ethyl acetate (20 mL, 5 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/70→10/90), and fractions containing the object product were concentrated under reduced pressure. The obtained residue was recrystallized from tetrahydrofuran and ethanol to give the title compound (169 mg, 87%) as colorless crystals.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate (20 mL, 5 mL)
  2. washThe combined organic layer was washed with saturated brine (5 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/70→10/90), and fractions
  7. additioncontaining the object product
  8. concentrationwere concentrated under reduced pressure
  9. customThe obtained residue was recrystallized from tetrahydrofuran and ethanol

Quellen und Nachweise

ORD-Eintrag
ord-bce0611ff79c49c4894ad581e825ed68
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08344135B2

Notizen zur Reaktion

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