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Diisopropylethylamine → HCID 58024764, Verbindung

HRID 1675680
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1675680
[NH2:1][CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[N:7][C:6]2[N:11]([CH2:14][CH3:15])[N:12]=[CH:13][C:5]=2[C:4]=1[NH:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[CH3:23][C:24]([O:27][C:28]([NH:30][C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](O)=[O:34])=[O:29])([CH3:26])[CH3:25].C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C)C=O>[CH2:14]([N:11]1[C:6]2=[N:7][C:8]([CH2:9][CH3:10])=[C:3]([CH2:2][NH:1][C:33]([C:32]3[CH:36]=[CH:37][CH:38]=[CH:39][C:31]=3[NH:30][C:28](=[O:29])[O:27][C:24]([CH3:25])([CH3:23])[CH3:26])=[O:34])[C:4]([NH:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:5]2[CH:13]=[N:12]1)[CH3:15]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOP2×HCID 4087778Boc-2-Abz-OHHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Produkt 1

HCID 58024764HCID 58024764, VerbindungAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of Intermediate 7 (250 mg, 0,83 mmol) and 2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)benzoic acid (196 mg, 0.83 mmol, e.g. available from Fluka) in N,N-dimethylformamide (4 ml) was treated with N,N-diisopropylethylamine (0.569 ml, 3.3 mmol) and (1H-1,2,3-benzotriazol-1-yloxy)(tri-1-pyrrolidinyl)phosphonium hexafluorophosphate (472 mg, 0.91 mmol) and allowed to stir at room temperature for 4 hours. An additional portion of (1H-1,2,3-benzotriazol-1-yloxy)(tri-1-pyrrolidinyl)phosphonium hexafluorophosphate (0.5 equiv., 0.41 mmol) was added and the mixture stirred for an additional hour. The solvent was evaporated and the residue dissolved in ethyl acetate (50 ml) and washed with aqueous sodium bicarbonate solution (2×50 ml); the organic fraction was dried (Na2SO4) and evaporated. The residue was purified by chromatography on silica gel (50 g SPE cartridge), eluting with a gradient of 0-100% ethyl acetate/cyclohexane followed by a gradient of 0-20% methanol/ethyl acetate over 40 minutes. Fractions containing product were pooled and evaporated to give the title compound (292 mg). LCMS showed MH+=523; TRET=2.71 min.

Aufarbeitung

  1. stirringthe mixture stirred for an additional hour
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in ethyl acetate (50 ml)
  4. washwashed with aqueous sodium bicarbonate solution (2×50 ml)
  5. dry with materialthe organic fraction was dried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by chromatography on silica gel (50 g SPE cartridge)
  8. washeluting with a gradient of 0-100% ethyl acetate/cyclohexane
  9. waitfollowed by a gradient of 0-20% methanol/ethyl acetate over 40 minutes
  10. additionFractions containing product
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c99060666b21456d9d602e0ecc0eaeab
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08003663B2

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