Diisopropylethylamine → 3-{1-[(3-fluoro-2-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}thieno[3,2-c]pyridin-4-amine

HRID 1909963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909963
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:14]4[C:15]([NH2:19])=[N:16][CH:17]=[CH:18][C:13]=4[S:12][CH:11]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:44][C:45]1[C:46]([CH3:55])=[C:47]([CH2:51][C:52](O)=[O:53])[CH:48]=[CH:49][CH:50]=1.CCN(C(C)C)C(C)C>O.CN(C)C=O>[F:44][C:45]1[C:46]([CH3:55])=[C:47]([CH2:51][C:52]([N:1]2[C:9]3[C:4](=[CH:5][C:6]([C:10]4[C:14]5[C:15]([NH2:19])=[N:16][CH:17]=[CH:18][C:13]=5[S:12][CH:11]=4)=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[O:53])[CH:48]=[CH:49][CH:50]=1

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 27792472-(3-Fluoro-2-methylphenyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668235693-(2,3-dihydro-1H-indol-5-yl)thieno[3,2-c]pyridin-4-amine

Produkt 1

HCID 534673873-{1-[(3-fluoro-2-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}thieno[3,2-c]pyridin-4-amineAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a 4 mL screw cap vial was added 3-(2,3-dihydro-1H-indol-5-yl)thieno[3,2-c]pyridin-4-amine (100 mg, 0.329 mmol) followed by HATU (125 mg, 0.329 mmol), 3-Fluoro-2-methylphenyl acetic acid (55.4 mg, 0.329 mmol) and DIEA (0.230 mL, 1.317 mmol). N,N-Dimethylformamide (DMF) (2 mL) was added and the reaction was sealed and left to stir at room temperature overnight. The reaction mixture was poured into water (4 mL) and extracted with EtOAc (5 mL). The organics were dried over Na2SO4 and concentrated. The residue was taken up in DCM and purified via normal phase chromatography (0-10% MeOH/DCM). Fractions were collected and concentrated to afford 3-{1-[(3-fluoro-2-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}thieno[3,2-c]pyridin-4-amine (94.6 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.12 (d, J=8.1 Hz, 1H) 7.83 (d, J=5.8 Hz, 1H) 7.41 (s, 1H) 7.35 (s, 1H) 7.26 (d, J=5.6 Hz, 1H) 7.14-7.25 (m, 2H) 7.02-7.11 (m, 2H) 5.42 (br. s., 2H) 4.31 (t, J=8.5 Hz, 2H) 3.97 (s, 2H) 3.27 (t, 2H) 2.15 (m, 3H).

Aufarbeitung

  1. customTo a 4 mL screw cap
  2. customthe reaction was sealed
  3. waitleft
  4. extractionextracted with EtOAc (5 mL)
  5. dry with materialThe organics were dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified via normal phase chromatography (0-10% MeOH/DCM)
  8. customFractions were collected
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a8aa651484f44b02866acfa4c1e2e60c
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598156B2

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