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Hydrochloric Acid → 2-[(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-N-(4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-nicotinamide

HRID 2247298
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2247298
C(OC([N:8]1[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]2[C:10](=[CH:11][C:12]([NH:20][C:21]([C:23]3[C:24]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][N:34]=[C:33]5[NH:37][CH2:38][CH2:39][C:32]=45)=[N:25][CH:26]=[CH:27][CH:28]=3)=[O:22])=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1>[NH:37]1[C:33]2=[N:34][CH:35]=[CH:36][C:31]([CH2:30][NH:29][C:24]3[N:25]=[CH:26][CH:27]=[CH:28][C:23]=3[C:21]([NH:20][C:12]3[CH:11]=[C:10]4[C:15]([C:16]([CH3:19])([CH3:18])[CH2:17][NH:8][CH2:9]4)=[CH:14][CH:13]=3)=[O:22])=[C:32]2[CH2:39][CH2:38]1
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Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20773481tert-Butyl 7-[({2-[(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)amino]pyridin-3-yl}carbonyl)amino]-4,4-dimethyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Produkt 1

HCID 103878712-[(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-N-(4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 7-({2-[(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-pyridine-3-carbonyl}-amino)-4,4-dimethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.070 g), HCl (4N, 3.0 mL) and dioxane (4.0 mL) was stirred at RT for overnight. Sat'd NaHCO3 was added until the bubbling stopped. The aqueous phase was extracted with CH2Cl2 3 times. The combined organic phases were dried over Na2SO4 and evaporated to yield a tan colored residue as a crude product, which was chromatographed through HPLC. The fractions were collected and the solvent was evaporated. The residue was treated with NaHCO3 and the solvent was evaporated. The residue was washed with H2O to remove any inorganics to afford 2-[(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)-amino]-N-(4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-nicotinamide.

Aufarbeitung

  1. extractionThe aqueous phase was extracted with CH2Cl2 3 times
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customevaporated
  4. customto yield a tan colored residue as a crude product, which
  5. customwas chromatographed through HPLC
  6. customThe fractions were collected
  7. customthe solvent was evaporated
  8. additionThe residue was treated with NaHCO3
  9. customthe solvent was evaporated
  10. washThe residue was washed with H2O
  11. customto remove any inorganics

Quellen und Nachweise

ORD-Eintrag
ord-d03e232ec0224732b7f07e135aacf3bc
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07687643B2

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