N-Methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine → Tofacitinib

HRID 1594375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594375
[CH3:1][N:2]([C@@H:12]1[C@H:17]([CH3:18])[CH2:16][CH2:15][NH:14][CH2:13]1)[C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1.O=C1CCC(=O)N1[O:26][C:27](=O)[CH2:28][C:29]#[N:30]>C(O)C>[CH3:18][C@@H:17]1[CH2:16][CH2:15][N:14]([C:27](=[O:26])[CH2:28][C:29]#[N:30])[CH2:13][C@@H:12]1[N:2]([CH3:1])[C:3]1[C:4]2[CH:11]=[CH:10][NH:9][C:5]=2[N:6]=[CH:7][N:8]=1

Komponenten

4

Edukt 2

HCID 23401507N-Methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amineHCID 534158962,5-Dioxopyrrolidin-1-yl 2-cyanoacetate

Produkt 1

HCID 9926791TofacitinibAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of the product from Method B (1.0 g) dissolved in 30 mL of ethanol was added 0.82 g of cyano-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester and the resulting mixture stirred at room temperature for 2 h. The reaction mixture was filtered through Celite® and concentrated in vacuo. The residue was redissolved in dichloromethane, washed with saturated, aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated to dryness in vacuo affording 1.1 g (86%) of the title compound as a yellow foam. LRMS: 313 (M+1).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite®
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washwashed with saturated, aqueous sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fab41313f5474ba3a29c20fae2961a36
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07301023B2

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