Trifluoroacetic acid → N-[[(2S)-1-benzylpyrrolidin-2-yl]methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

HRID 589982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 589982
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][N:14](C(OC(C)(C)C)=O)[S:15]([N:18]1[C:23]2([CH2:25][CH2:24]2)[CH2:22][N:21]([C:26]2[C:27]3[CH:34]=[CH:33][N:32](C(OC(C)(C)C)=O)[C:28]=3[N:29]=[CH:30][N:31]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][S:15]([N:18]1[C:23]2([CH2:24][CH2:25]2)[CH2:22][N:21]([C:26]2[C:27]3[CH:34]=[CH:33][NH:32][C:28]=3[N:29]=[CH:30][N:31]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 68296033tert-butyl 4-[8-[[(2S)-1-benzylpyrrolidin-2-yl]methyl-tert-butoxycarbonyl-sulfamoyl]-5,8-diazaspiro[2.5]octan-5-yl]pyrrolo[2,3-d]pyrimidine-7-carboxylate2×

Produkt 1

HCID 57411876N-[[(2S)-1-benzylpyrrolidin-2-yl]methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-butyl 4-[8-[[(2S)-1-benzylpyrrolidin-2-yl]methyl-tert-butoxycarbonyl-sulfamoyl]-5,8-diazaspiro[2.5]octan-5-yl]pyrrolo[2,3-d]pyrimidine-7-carboxylate (Intermediate 48) (0.57 mmol) was dissolved in DCM (10 mL) and added TFA (1 mL). The reaction mixture was stirred at rt for 16 h, then added NaHCO3 (15 mL) and extracted with EtOAc (2×25 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica using EtOAc and MeOH in heptane as eluent.

Aufarbeitung

  1. extractionadded NaHCO3 (15 mL) and extracted with EtOAc (2×25 mL)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-75bd5104d5b142e58c413a13002aafd9
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233964B2

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