Diisopropylethylamine → 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 570393

Reaktionsgleichung

Reaktionsgleichung von HRID 570393
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][C:9]([NH:10][C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:16]([OH:18])=O)=[C:4]2[CH:3]=[CH:2]1.C(N(C(C)C)CC)(C)C.[C:28]([N:35]1[CH2:39][CH2:38][CH:37]([NH2:40])[CH2:36]1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.C(OCC)(=O)C>[C:31]([O:30][C:28]([N:35]1[CH2:39][CH2:38][CH:37]([NH:40][C:16]([C:12]2[S:13][CH:14]=[CH:15][C:11]=2[NH:10][C:9]2[CH:8]=[CH:7][N:6]=[C:5]3[NH:1][CH:2]=[CH:3][C:4]=23)=[O:18])[CH2:36]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 27563701-Boc-3-aminopyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669574403-(1H-pyrrolo[2,3-b]pyridin-4-ylamino)thiophene-2-carboxylic acid

Produkt 1

HCID 669579823-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carboxylic acid (100 mg, 0.39 mmol), diisopropylethylamine (0.1 mL, 0.54 mmol), 1-BOC-3-aminopyrrolidine (143 mg, 0.77 mmol) in dimethylformamide (2 mL) was added HATU (176 mg, 0.463 mmol). The solution stirred at room temperature for 18 h then diluted with ethyl acetate and washed with aqueous 1% lithium chloride. The organic layer was dried, concentrated in vacuo and purified by ISCO Companion to provide 3-{[3-(1H-Pyrrolo[2,3-b]pyridin-4-ylamino)-thiophene-2-carbonyl]-amino}-pyrrolidine-1-carboxylic acid tert-butyl ester (161 mg, 95%). LCMS (ESI) 428 (M+H) 1H NMR (400 MHz, DMSO-d6) δ ppm 11.55 (1H, br. s.) 10.24 (1H, s) 8.20 (1H, d, J=6.83 Hz) 8.02 (1H, d, J=5.47 Hz) 7.81 (1H, d, J=5.47 Hz) 7.47 (1H, d, J=5.47 Hz) 7.31 (1H, dd, J=3.32, 2.54 Hz) 6.80 (1H, d, J=5.47 Hz) 6.44 (1H, dd, J=3.42, 1.85 Hz) 4.35-4.58 (1H, m) 3.47-3.65 (1H, m) 3.33-3.44 (1H, m) 3.26 (1H, t, J=9.08 Hz) 3.09-3.21 (1H, m) 1.99-2.14 (1H, m) 1.81-1.95 (1H, m) 1.39 (9H, s).

Aufarbeitung

  1. washwashed with aqueous 1% lithium chloride
  2. customThe organic layer was dried
  3. concentrationconcentrated in vacuo
  4. custompurified by ISCO Companion

Quellen und Nachweise

ORD-Eintrag
ord-025ba6e5600d4ea19742520ac2f532ab
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023847B2

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