Toluene → (+/-)-5-(1-(2-azaspiro[3.3]heptan-6-yl)-1H-pyrazol-4-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine formate

HRID 587114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587114
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH:13]3[CH2:26][C:15]4([CH2:18][N:17]([C:19]([O:21]C(C)(C)C)=[O:20])[CH2:16]4)[CH2:14]3)[CH:12]=2)=[CH:4][C:3]=1[O:27][CH:28]([C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[C:32]([F:37])[C:31]=1[Cl:38])[CH3:29].C1(C)C=CC=CC=1>C(O)=O>[CH:19]([OH:21])=[O:20].[CH2:16]1[C:15]2([CH2:14][CH:13]([N:11]3[CH:12]=[C:8]([C:5]4[CH:4]=[C:3]([O:27][CH:28]([C:30]5[C:35]([Cl:36])=[CH:34][CH:33]=[C:32]([F:37])[C:31]=5[Cl:38])[CH3:29])[C:2]([NH2:1])=[N:7][CH:6]=4)[CH:9]=[N:10]3)[CH2:26]2)[CH2:18][NH:17]1

Komponenten

4

Edukt 2

HCID 1140TolueneHCID 71240178tert-Butyl 6-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)-2-azaspiro[3.3]heptane-2-carboxylate

Produkt 1

HCID 71240904(+/-)-5-(1-(2-azaspiro[3.3]heptan-6-yl)-1H-pyrazol-4-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine formateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

tert-Butyl 6-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)-2-azaspiro[3.3]heptane-2-carboxylate (53 mg, 0.094 mmol) was dissolved in formic acid (3 mL). The solution was sonicated at room temperature for 1.0 h and then concentrated by evaporation in vacuo to give the residue. Toluene (2×5 mL) was added and evaporated again. Ether (10 mL) was added and the mixture was stirred at room temperature for 1.0 h. The solid was collected by filtration, washed with ether (10 mL) and then dried under high vacuum to afford (±)-5-(1-(2-azaspiro[3.3]heptan-6-yl)-1H-pyrazol-4-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine formate (29 mg, 61%) as an off-white solid.

Aufarbeitung

  1. customThe solution was sonicated at room temperature for 1.0 h
  2. concentrationconcentrated by evaporation in vacuo
  3. customto give the residue
  4. customevaporated again
  5. additionEther (10 mL) was added
  6. filtrationThe solid was collected by filtration
  7. washwashed with ether (10 mL)
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-019cd14794f14122bfeccae7b00f3123
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226923B2

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