Diisopropylethylamine → 1-((4-Cyanophenyl)(8-methoxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 517180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517180
F[B-](F)(F)F.[CH3:6][O+](C)C.[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:33]2[C:43](=[O:44])[CH2:42][C:36]3([CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH2:35][C:34]=2[OH:45])[NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)=[O:21])=[CH:14][CH:13]=1)#[N:11].C(N(CC)C(C)C)(C)C>ClCCl>[C:10]([C:12]1[CH:13]=[CH:14][C:15]([CH:18]([C:33]2[C:34](=[O:45])[CH2:35][C:36]3([CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)[CH2:42][C:43]=2[O:44][CH3:6])[NH:19][C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)=[O:21])=[CH:16][CH:17]=1)#[N:11]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 867322991-((4-Cyanophenyl)(8-hydroxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea2×

Produkt 1

HCID 867323001-((4-Cyanophenyl)(8-methoxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trimethyloxonium tetrafluoroborate (320 mg, 2.16 mmol) is added to a solution of 1-((4-cyanophenyl)(8-hydroxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea (intermediate 10, 712 mg, 1.43 mmol) and N,N-diisopropylethylamine (490 μL, 2.81 mmol) in dichloromethane (20 mL). The mixture is stirred at room temperature for 30 min and washed with water. The organic layer is concentrated under reduced pressure, and the residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 380 mg; ESI mass spectrum [M+H]+=514, Retention time HPLC: 1.18 min (V012_S01).

Aufarbeitung

  1. washwashed with water
  2. concentrationThe organic layer is concentrated under reduced pressure
  3. customthe residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  4. custom1.18 min (V012_S01)

Quellen und Nachweise

ORD-Eintrag
ord-2fac46ab36e747adb8665253079ec841
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115093B2

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