Acetic Acid → HCID 66738579, Verbindung

HRID 2047208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047208
[CH3:1][C@@H:2]1[CH2:7][CH:6]([NH2:8])[CH2:5][C@H:4]([CH3:9])[O:3]1.[CH3:10][Si:11]([CH3:49])([CH3:48])[CH2:12][CH2:13][O:14][CH2:15][N:16]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:17]1[N:22]2[N:23]=[CH:24][C:25]([C:26]3[CH:27]=[N:28][C:29]4[C:34]([CH:35]=3)=[CH:33][C:32]([F:36])=[CH:31][CH:30]=4)=[C:21]2[N:20]=[C:19]([CH:37]=O)[C:18]=1[Br:39].CC(O)=O.[BH3-]C#N.[Na+]>ClCCCl.C(O)C.C(Cl)Cl>[Br:39][C:18]1[C:19]([CH2:37][NH:8][CH:6]2[CH2:5][C@H:4]([CH3:9])[O:3][C@H:2]([CH3:1])[CH2:7]2)=[N:20][C:21]2[N:22]([N:23]=[CH:24][C:25]=2[C:26]2[CH:27]=[N:28][C:29]3[C:34]([CH:35]=2)=[CH:33][C:32]([F:36])=[CH:31][CH:30]=3)[C:17]=1[N:16]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:45])([CH3:46])[CH3:47])[CH2:15][O:14][CH2:13][CH2:12][Si:11]([CH3:48])([CH3:49])[CH3:10]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 667335321251772-69-6HCID 86664791HCID 86664791, Verbindung

Produkt 1

HCID 66738579HCID 66738579, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 702EthanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To crude (2R,6S)-2,6-dimethyltetrahydro-2H-pyran-4-amine (0.18 g) in DCE (4.2 ml) and Ethanol (4.2 ml) was added 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidine-5-carbaldehyde (0.19 g, 0.3 mmol) followed by AcOH (0.03 ml, 0.6 mmol). After stirring for 30 minutes at room temperature, NaBH3CN (37.8 mg, 0.6 mmol) was added and stirring was continued further for 30 minutes more. LC/MS showed no starting material remaining. After the solvent was rotoevaporated, the crude was dissolved with DCM (20 ml), washed with sat. NaHCO3 (1×5 ml), water (1×5 ml), brine (1×5 ml), dried over MgSO4. Solvent was removed in vacuo and the residue was purified by column chromatography on silica gel. Elution with EtOAc/Hexanes (0-60%) gave desired 6-bromo-5-(((2R,6S)-2,6-dimethyltetrahydro-2H-pyran-4-ylamino)methyl)-3-(6-fluoroquinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (68 mg, 30%).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued further for 30 minutes
  3. washwashed with sat. NaHCO3 (1×5 ml), water (1×5 ml), brine (1×5 ml)
  4. dry with materialdried over MgSO4
  5. customSolvent was removed in vacuo
  6. customthe residue was purified by column chromatography on silica gel
  7. washElution with EtOAc/Hexanes (0-60%)

Quellen und Nachweise

ORD-Eintrag
ord-7f0159e39aae4f298948814ab096e6f9
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591943B2

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