Diisopropylethylamine → HCID 178485569, Verbindung

HRID 2279904Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2279904
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:36]=[CH:35][C:27]([CH2:28][CH2:29][CH:30]([PH:32](=[O:34])[OH:33])[CH3:31])=[CH:26][C:25]=3[O:37][CH3:38])[N:14]=2)=[CH:4][CH:3]=1.[CH3:39][C:40]1([CH3:56])[C:44]([CH3:46])([CH3:45])[O:43][B:42]([C:47]2[CH:48]=[N:49][N:50]([CH2:52][CH2:53][CH2:54]O)[CH:51]=2)[O:41]1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>ClCCCl>[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:11])[NH:9][CH3:10])[C:5]([NH:12][C:13]2[C:18]([C:19]([F:22])([F:20])[F:21])=[CH:17][N:16]=[C:15]([NH:23][C:24]3[CH:36]=[CH:35][C:27]([CH2:28][CH2:29][CH:30]([PH:32](=[O:33])[O:34][CH2:54][CH2:53][CH2:52][N:50]4[CH:51]=[C:47]([B:42]5[O:43][C:44]([CH3:46])([CH3:45])[C:40]([CH3:39])([CH3:56])[O:41]5)[CH:48]=[N:49]4)[CH3:31])=[CH:26][C:25]=3[O:37][CH3:38])[N:14]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 671871273-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol2×HCID 178485565HCID 178485565, Verbindung2×

Produkt 1

HCID 178485569HCID 178485569, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of (4-{[4-{[6-bromo-2-(methylcarbamoyl)pyridin-3-yl]amino}-5-(trifluoromethyl)pyrimidin-2-yl]amino}-3-methoxybenzyl)propan-2-ylphosphinic acid (Compound 68B, 0.240 g, 0.389 mmol) and 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol (Compound 3E, 97.9 g, 0.388 mmol) in 1,2-dichloroethane (8.53 mL) and DIPEA (0.812 mL, 4.66 mmol) was charged with (benzotriazol-1-yloxy)tripyrrolidino-phosphonium hexafluorophosphate (1.21 g, 2.33 mmol). The reaction mixture was stirred at 60° C. for 16 hours. The reaction mixture was quenched with water (10 mL) and extracted with DCM (20 mL). The organic layer was washed with NaHCO3 (10 mL), washed with brine (15 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to a brown oil. The crude material was purified using a Teledyne ISCO Combiflash® Rf system using 1:1 DCM-EtOAc/MeOH (100:0→90:10) as eluent to afford the title compound as an off-white foam. MS (ESI): m/z 851.84/853.82 [M+H]+. UPLC: tR=1.57 min (UPLC-SQD: analytical—2 min).

Aufarbeitung

  1. customThe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with DCM (20 mL)
  3. washThe organic layer was washed with NaHCO3 (10 mL)
  4. washwashed with brine (15 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to a brown oil
  8. customThe crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-b7b12b9807bd4852a7c9f65f15a63b12
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133224B2

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