Pyridine → HCID 71768587, Verbindung

HRID 2272271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272271
[NH:1]1[CH2:4][CH:3]([CH2:5][CH2:6][N:7]([S:31]([CH3:34])(=[O:33])=[O:32])[C:8]2[C:9]([CH:28]3[CH2:30][CH2:29]3)=[CH:10][C:11]3[C:15]([CH:16]=2)=[N:14][N:13]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:12]=3[C:24]([NH:26][CH3:27])=[O:25])[CH2:2]1.[C:35](OC(=O)C)(=[O:37])[CH3:36].N1C=CC=CC=1>C(Cl)Cl>[C:35]([N:1]1[CH2:4][CH:3]([CH2:5][CH2:6][N:7]([S:31]([CH3:34])(=[O:33])=[O:32])[C:8]2[C:9]([CH:28]3[CH2:29][CH2:30]3)=[CH:10][C:11]3[C:15]([CH:16]=2)=[N:14][N:13]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[C:12]=3[C:24]([NH:26][CH3:27])=[O:25])[CH2:2]1)(=[O:37])[CH3:36]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 717690346-{[2-(Azetidin-3-yl)ethyl](methylsulfonyl)amino}-2-(4-chlorophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide

Produkt 1

HCID 71768587HCID 71768587, VerbindungAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of Compound (6) (8 mg, 0.02 mmol) in DCM (2.0 mL) was added acetic anhydride (0.1 mL) and pyridine (0.1 mL) and the mixture was stirred at ambient temperature for 16 h. The reaction mixture was then concentrated in vacuo and the residue partitioned between EtOAc (25 mL) and water (15 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (3×15 mL). The combined organics were washed with brine (15 mL), dried (MgSO4) and concentrated in vacuo (32 mg). The crude material was purified by reverse phase preparative LCMS: Acetonitrile/water (0.1% formic acid) to give Compound (8) (2.14 mg, 20%). ESI-MS m/z calculated for [M+H]+: 544.2. found: 544.1. 1H NMR (400 MHz, CD3CN) δ 7.85 (s, 1H), 7.63-7.54 (m, 4H), 7.40 (s, 1H), 7.05 (br s, 1H), 4.21-4.14 (m, 1H), 3.93 (td, J=8.9, 3.2 Hz, 1H), 3.76-3.67 (m, 3H), 3.49-3.43 (m, 1H), 3.11 (d, J=1.0 Hz, 3H), 2.93 (d, J=4.8 Hz, 3H), 2.77-2.64 (m, 1H), 2.46-2.36 (m, 1H), 1.95-1.81 (m, 2H), 1.73 (d, J=2.4 Hz, 3H), 1.14-1.02 (m, 3H), 0.69-0.58 (m, 1H).

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned between EtOAc (25 mL) and water (15 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc (3×15 mL)
  5. washThe combined organics were washed with brine (15 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo (32 mg)
  8. customThe crude material was purified by reverse phase preparative LCMS

Quellen und Nachweise

ORD-Eintrag
ord-b3c19a070e364ebd93a4a285ff663bf7
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120775B2

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