Diisopropylethylamine → 3-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

HRID 627343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627343
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=C[CH:44]=[CH:45][C:40]=2N=N1.[CH:54](N(CC)C(C)C)(C)C.[CH:63]12[N:70]([C:71]([OH:73])=[O:72])[CH:67]([CH2:68][CH2:69]1)[CH2:66][NH:65][CH2:64]2>CN(C=O)C.CCOC(C)=O>[C:45]([O:72][C:71]([N:70]1[CH:63]2[CH2:69][CH2:68][CH:67]1[CH2:66][N:65]([C:20]([C:19]1[CH:18]=[N:17][C:16]([NH:15][C:12]3[N:13]=[CH:14][C:9]4[CH:8]=[C:7]([C:25](=[O:29])[N:26]([CH3:27])[CH3:28])[N:6]([CH:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)[C:10]=4[N:11]=3)=[CH:24][CH:23]=1)=[O:22])[CH2:64]2)=[O:73])([CH3:44])([CH3:40])[CH3:54]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222733513,8-Diaza-bicyclo[3.2.1]octane-8-carboxylic acidHCID 583154726-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid

Produkt 1

HCID 673560653-[6-(7-Cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridine-3-carbonyl]-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid (400 mg, 1.01 mmol) in DMF (5 mL) was added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU, 580 mg, 1.53 mmol, 1.5 equiv) and N,N-diisopropylethylamine (0.55 mL, 3.0 equiv) and the resulting mixture stirred at room temperature for 5 minutes. To the reaction mixture was added 3,8-Diaza-bicyclo[3.2.1]octane-8-carboxylic acid Pert-butyl ester (250 mg, 1.18 mmol. 1.1 eq). The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted in EtOAc, washed with 0.5M HCl, water, dried over Na2SO4, filtered and concentrated. Material was immediately used in next step without further purification. MS: (M+H)=589.7

Aufarbeitung

  1. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  2. washwashed with 0.5M HCl, water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customMaterial was immediately used in next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-61f6e2312e3f4225b69cfbebc79afb54
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309252B2

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