Potassium Fluoride → 3-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-propionic acid

HRID 1926354

Reaktionsgleichung

Reaktionsgleichung von HRID 1926354
C[O:2][C:3](=[O:12])[CH2:4][CH2:5][N:6]1[CH:10]=[C:9](I)[CH:8]=[N:7]1.[S:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[C:14]1[C:22]1[C:23]([NH2:37])=[N:24][CH:25]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:27]=1.[F-].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1.O>[NH2:37][C:23]1[N:24]=[CH:25][C:26]([C:9]2[CH:8]=[N:7][N:6]([CH2:5][CH2:4][C:3]([OH:2])=[O:12])[CH:10]=2)=[CH:27][C:22]=1[C:14]1[S:13][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=1

Komponenten

6

Edukt 3

HCID 522689Potassium FluorideHCID 574165133-(1,3-Benzothiazol-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 64435500methyl 3-(4-iodo-1H-pyrazol-1-yl)propanoate

Produkt 1

HCID 675206793-[4-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-pyrazol-1-yl]-propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 3-(4-iodopyrazol-1-yl)-propionic acid methyl ester (174 mg, 0.623 mmol), 3-benzothiazol-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridin-2-ylamine (200.0 mg, 0.5662 mmol), Pd(PPh3)4 (50 mg, 0.04 mmol), potassium fluoride (98.7 mg, 1.70 mmol), and 4:1 dioxane:water (4:1, 1,4-dioxane:H2O, 8 mL) was heated in the microwave reactor at 85° C. for 30 min. The solution was concentrated in vacuo, and dry-loaded onto silica gel for column chromatography. The material was eluted with 2% MeOH/DCM. The fractions containing the product were concentrated in vacuo. The material was dissolved in conc. HCl (4 mL) and heated to 60° C. for 30 min in a sealed tube. The solvent was removed using the corrosive pump to afford the title compound as an orange solid. MS (ES+): m/z=366.14 (100) [MH+]. HPLC: tR=2.59 min (ZQ2, polar—5 min).

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. washThe material was eluted with 2% MeOH/DCM
  3. additionThe fractions containing the product
  4. concentrationwere concentrated in vacuo
  5. dissolutionThe material was dissolved in conc. HCl (4 mL)
  6. temperatureheated to 60° C. for 30 min in a sealed tube
  7. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-5e4425b3616a42a39d65f004d4be6c43
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178668B2

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