Triethylamine → N-{5-[(7-tert-Butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}-2-(5-fluoropyridin-2-yl)acetamide

HRID 82081

Reaktionsgleichung

Reaktionsgleichung von HRID 82081
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=O)=[N:6][CH:7]=1.[NH2:12][C:13]1[CH:14]=[C:15]([C:19]([C:21]2[C:29]3[CH:28]=[N:27][CH:26]=[N:25][C:24]=3[N:23]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:22]=2)=[O:20])[CH:16]=[N:17][CH:18]=1.CCCP(O)(O)=O.C(N(CC)CC)C>C1COCC1>[C:30]([N:23]1[C:24]2[N:25]=[CH:26][N:27]=[CH:28][C:29]=2[C:21]([C:19]([C:15]2[CH:14]=[C:13]([NH:12][C:9](=[O:11])[CH2:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=3)[CH:18]=[N:17][CH:16]=2)=[O:20])=[CH:22]1)([CH3:33])([CH3:31])[CH3:32]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 204484Propylphosphonic acidHCID 55267809(5-Fluoropyridin-2-yl)acetic acidHCID 70817490(5-aminopyridin-3-yl)(7-tert-butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

Produkt 1

HCID 70818020N-{5-[(7-tert-Butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}-2-(5-fluoropyridin-2-yl)acetamideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2-(5-Fluoropyridin-2-yl)acetic acid (23.1 mg, 0.149 mmol) (see Preparation 92) was added to (5-aminopyridin-3-yl)(7-tert-butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone (40 mg, 0.135 mmol) (see Preparation 31), 1-propylphosphonic acid cyclic anhydride (0.2 mL, 0.338 mmol, 50% in EtOAc) and triethylamine (0.65 mL, 0.474 mmol) in THF (3 mL). The mixture was stirred at 25° C. for 18 hours, evaporated in vacuo and partitioned between saturated aqueous sodium bicarbonate (5 mL) and ethyl acetate (5 mL). The organic phase was dried over sodium sulfate, evaporated in vacuo and the residue was triturated with pentane:diethyl ether (3:1, 1 mL) to afford the title compound as an off white solid in 65% yield, 38 mg.

Aufarbeitung

  1. customevaporated in vacuo
  2. custompartitioned between saturated aqueous sodium bicarbonate (5 mL) and ethyl acetate (5 mL)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated in vacuo
  5. customthe residue was triturated with pentane:diethyl ether (3:1, 1 mL)

Quellen und Nachweise

ORD-Eintrag
ord-565c04c6b64d4925893feadacda4d812
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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