Diisopropylethylamine → 3-{1-[(3-chloro-2,4-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1910036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910036
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:19]4[C:14](=[N:15][CH:16]=[N:17][C:18]=4[NH2:20])[N:13]([CH3:21])[N:12]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[Cl:22][C:23]1[C:24]([F:34])=[C:25]([CH2:30][C:31](O)=[O:32])[CH:26]=[CH:27][C:28]=1[F:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Cl:22][C:23]1[C:24]([F:34])=[C:25]([CH2:30][C:31]([N:2]2[C:10]3[C:5](=[CH:6][C:7]([C:11]4[C:19]5[C:14](=[N:15][CH:16]=[N:17][C:18]=5[NH2:20])[N:13]([CH3:21])[N:12]=4)=[CH:8][CH:9]=3)[CH2:4][CH2:3]2)=[O:32])[CH:26]=[CH:27][C:28]=1[F:29]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 177508243-Chloro-2,4-difluorobenzeneacetic acidHCID 668238703-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine HCl

Produkt 1

HCID 668237563-{1-[(3-chloro-2,4-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a 20 mL vial with cap, to a solution of 3-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine HCl (70 mg, 0.231 mmol), (3-chloro-2,4-difluorophenyl)acetic acid (47.8 mg 0.231 mmol), and HATU (88 mg, 0.231 mmol) in DMF (2 mL) was added Hunig's base (0.162 mL, 0.925 mmol). The mixture was stirred overnight. The reaction was poured into water (100 mL), and an off-white solid was formed. The solid was filtered, washed with water (10 mL), and dried to afford the title compound as an off-white solid. LC-MS (ES) m/z=455.4 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.24-3.31 (m, 2H), 3.94 (s, 3H), 4.03 (s, 2H), 4.32 (t, J=8.46 Hz, 2H), 7.30-7.36 (m, 1H), 7.39-7.46 (m, 2H), 7.54 (s, 1H), 8.14 (d, J=8.34 Hz, 1H), 8.25 (s, 1H).

Aufarbeitung

  1. customan off-white solid was formed
  2. filtrationThe solid was filtered
  3. washwashed with water (10 mL)
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f7f31fa5b85849d2b8cecd6fa607cd3f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598156B2

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