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2-(Benzenesulfonyl)-3-phenyloxaziridine → Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate

HRID 1400753
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1400753
C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1C[O:14]CC1.[CH2:16]([O:19][C:20]1([CH3:49])[CH2:25][CH2:24][N:23]([C:26]2[N:31]3[N:32]=[C:33]([C:35]4[CH:40]=[CH:39][CH:38]=[C:37]([Br:41])[CH:36]=4)[CH:34]=[C:30]3[N:29]=[C:28]([CH3:42])[C:27]=2[CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:22][CH2:21]1)[CH:17]=[CH2:18].C1(C2ON2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C1COCC1>[CH2:16]([O:19][C:20]1([CH3:49])[CH2:25][CH2:24][N:23]([C:26]2[N:31]3[N:32]=[C:33]([C:35]4[CH:40]=[CH:39][CH:38]=[C:37]([Br:41])[CH:36]=4)[CH:34]=[C:30]3[N:29]=[C:28]([CH3:42])[C:27]=2[CH:43]([OH:14])[C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:22][CH2:21]1)[CH:17]=[CH2:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 86624818Khmds thfHCID 86710809Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

Produkt 1

HCID 86710811Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetateAusbeute 82,6 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of 1M KHMDS/THF (49.3 mL, 49.3 mmol) in THF (150 mL) at −78° C. was added dropwise a THF (100 mL) solution of ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (20 g, 37.9 mmol) over 5 min. After 30 min, a THF (100 mL) solution of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (12.88 g, 49.3 mmol) was added and stirred for additional 30 min at −78° C. Then, the resulting dark reaction mixture was quenched with sat. NH4Cl (50 mL), diluted with EtOAc (200 mL), washed with water (100 mL), brine (100 mL), dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage(5-50% EtOAc/hexane) to afford ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(3-bromophenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (17 g, 31.3 mmol, 82% yield) as white foam. Impurities were present by NMR. Used as is in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 8.16 (t, J=1.7 Hz, 1H), 7.99-7.92 (m, 1H), 7.58-7.50 (m, 2H), 7.34 (t, J=7.9 Hz, 1H), 6.83 (s, 1H), 6.18-6.06 (m, 1H), 5.57 (d, J=5.4 Hz, 1H), 5.48 (d, J=17.0 Hz, 1H), 5.27 (d, J=10.2 Hz, 1H), 4.83 (br. s., 2H), 4.35 (dq, J=10.8, 7.1 Hz, 1H), 4.23 (dq, J=10.9, 7.1 Hz, 1H), 4.06-3.99 (m, 2H), 2.65 (s, 3H), 2.00 (d, J=14.2 Hz, 2H), 1.84 (d, J=13.4 Hz, 2H), 1.36 (s, 3H), 1.29-1.26 (m, 3H). LCMS (M+H)=545.3.

Aufarbeitung

  1. customThen, the resulting dark reaction mixture
  2. customwas quenched with sat. NH4Cl (50 mL)
  3. additiondiluted with EtOAc (200 mL)
  4. washwashed with water (100 mL), brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was then purified by Biotage(5-50% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-cd18bbd441dd4deca5e9b9211ea0eae4
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906929B2

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