Pyridine → Thiophene-2-carboxylic acid [2-methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl]-amide

HRID 536318

Reaktionsgleichung

Reaktionsgleichung von HRID 536318
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([N:9]2[CH2:13][CH2:12][C@@H:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[CH2:10]2)[N:3]=1.N1C=CC=CC=1.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](Cl)=[O:32].C(O)C(N)(CO)CO>ClCCCl>[CH3:1][C:2]1[C:7]([NH:8][C:31]([C:27]2[S:26][CH:30]=[CH:29][CH:28]=2)=[O:32])=[CH:6][CH:5]=[C:4]([N:9]2[CH2:13][CH2:12][C@@H:11]([N:14]3[CH2:18][CH2:17][CH2:16][C@@H:15]3[CH3:19])[CH2:10]2)[N:3]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6503Tris(hydroxymethyl)aminomethaneHCID 789282-Thiophenecarbonyl chlorideHCID 674804612-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]pyridin-3-amine

Produkt 1

HCID 54597155Thiophene-2-carboxylic acid [2-methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl]-amideAusbeute 23,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-methyl-6-[(3R)-3-[(2S)-2-methylpyrrolidin-1-yl]pyrrolidin-1-yl]pyridin-3-amine (22.7 mg, 0.09 mmol) in DCE (1 mL) was added pyridine (0.22 mL, 2.7 mmol) followed by a solution of thiophene-2-carbonyl chloride (40 mg, 0.27 mmol) in DCE (1 mL) and stirred at ambient temperature for 5 hours. To this mixture was then added trisamine resin (200 mg, 0.8 mmol, 4 mmol/g loading), stirred for 30 min, filtered and concentrated to afford a crude solid which was purified by flash column chromatography (5% 7N NH3 in MeOH/CH2Cl2) to obtain 7.8 mg of the title compound.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto afford a crude solid which
  4. customwas purified by flash column chromatography (5% 7N NH3 in MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-40bf7a6308f041999bcf5d056adc0e84
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859588B2

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