Acetic Acid → (S)-4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(5-(4-(3-methylbutan-2-yl)-4H-1,2,4-triazol-3-yl)thiophen-3-yl)picolinamide

HRID 2091625

Reaktionsgleichung

Reaktionsgleichung von HRID 2091625
[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH:17][C:18]4[CH:22]=[C:21]([C:23]([NH:25][NH2:26])=O)[S:20][CH:19]=4)=[O:16])[CH:10]=3)[CH:8]=2)[CH2:3][CH2:2]1.[CH3:27][CH:28]([CH3:32])[C@@H:29]([NH2:31])[CH3:30].[C:33](O)(=O)C>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH:17][C:18]4[CH:22]=[C:21]([C:23]5[N:31]([C@H:29]([CH:28]([CH3:32])[CH3:27])[CH3:30])[CH:33]=[N:26][N:25]=5)[S:20][CH:19]=4)=[O:16])[CH:10]=3)[CH:8]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 69997881,2-Dimethylpropylamine, (S)-HCID 580356454-(4-cyclopropyl-1H-imidazol-1-yl)-N-(5-(hydrazinecarbonyl)thiophen-3-yl)picolinamide

Produkt 1

HCID 56597393(S)-4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(5-(4-(3-methylbutan-2-yl)-4H-1,2,4-triazol-3-yl)thiophen-3-yl)picolinamideAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(5-(hydrazinecarbonyl)thiophen-3-yl)picolinamide (130 mg, 0.35 mmol) and toluene (2 mL) were added to a sealable vial. N,N-dimethylformamide/N,N-dimethylacetamide complex (120 μL, 0.88 mmol) was added and the reaction was stirred for 5 minutes. (S)-3-methylbutan-2-amine (170 μL, 1.4 mmol), and acetic acid (20 μL, 0.35 mmol) were added, and the reaction was heated in a microwave reactor at 150° C. for 30 minutes. The reaction was concentrated and purified by RP-HPLC to provide 65 mg (42%) of (S)-4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(5-(4-(3-methylbutan-2-yl)-4H-1,2,4-triazol-3-yl)thiophen-3-yl)picolinamide as a white solid.

Aufarbeitung

  1. additionwere added to a sealable vial
  2. additionN,N-dimethylformamide/N,N-dimethylacetamide complex (120 μL, 0.88 mmol) was added
  3. concentrationThe reaction was concentrated
  4. custompurified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-002925850de240dd8f25e7aaf84d5f55
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440665B2

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