Hydrochloric Acid → (4-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(cyclopropylsulfonyl)piperidin-4-yl)acetonitrile

HRID 1876854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876854
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:26][C:27]#[N:28])[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1.Cl.C(N(CC)CC)C.[CH:37]1([S:40](Cl)(=[O:42])=[O:41])[CH2:39][CH2:38]1>O1CCOCC1.C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]([C:13]3([CH2:26][C:27]#[N:28])[CH2:14][CH2:15][N:16]([S:40]([CH:37]4[CH2:39][CH2:38]4)(=[O:42])=[O:41])[CH2:17][CH2:18]3)[CH:12]=2)[CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 86637283tert-butyl 4-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidine-1-carboxylate

Produkt 1

HCID 86637287(4-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-1-(cyclopropylsulfonyl)piperidin-4-yl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a mixture of tert-butyl 4-(4-(2-chloropyrimidin-4-yl)-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidine-1-carboxylate (0.487 g, 1.21 mmol) in 2 mL of dioxane was added 4 M HCl in dioxane (4.0 mL). The reaction was stirred at room temperature for 30 min, then evaporated to dryness. To the resulting crude HCl salt in methylene chloride (9.4 mL) was added triethylamine (0.505 mL, 3.62 mmol) followed by cyclopropanesulfonyl chloride (0.148 mL, 1.45 mmol). The mixture was stirred at room temperature for 30 min, washed with saturated sodium bicarbonate, dried, and evaporated to dryness. The residue was used directly in next step (402 mg, 82%). LCMS (M+H) 407.0.

Aufarbeitung

  1. customevaporated to dryness
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. washwashed with saturated sodium bicarbonate
  4. customdried
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-4fff269e04d2425ab316c0d6a9f5568b
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309718B2

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