(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline → HCID 59536328, Verbindung

HRID 445282

Reaktionsgleichung

Reaktionsgleichung von HRID 445282
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.[N:21]1[CH:26]=[C:25]([NH:27][C:28](=O)[O:29]C2C=CC([N+]([O-])=O)=CC=2)[CH:24]=[N:23][CH:22]=1>CC#N>[N:21]1[CH:26]=[C:25]([NH:27][C:28]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:9]2[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=2)=[O:29])[CH:24]=[N:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinolineHCID 595363234-Nitrophenyl pyrimidin-5-ylcarbamate

Produkt 1

HCID 59536328HCID 59536328, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (100 mg, 0.30 mmol, example 30 (step 1)) and 4-nitrophenyl pyrimidin-5-ylcarbamate (93.8 mg, 0.36 mmol) in MeCN (3 mL) was heated to 70° C. overnight, and then was subjected to microwave irradiation at 120° C. for 15 min. The mixture was filtered and the filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give the title compound in solution of H2O (0.1% TFA) and MeCN (0.1% TFA). The solvent was partially removed and saturated NaHCO3 (10 mL) was added. The mixture was extracted with EtOAc (2×5 mL). The combined organic extracts were dried over MgSO4, concentrated, and dried in vacuo to give the title compound as a light yellow solid. MS (ESI, positive ion) m/z: 399 (M+H).

Aufarbeitung

  1. customirradiation at 120° C. for 15 min
  2. filtrationThe mixture was filtered
  3. customthe filtrate was purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-9fd39a58d785415fb0912f206d8b3213
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476297B2

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