Diisopropylethylamine → HCID 89722227, Verbindung

HRID 57718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57718
[CH3:1][O:2][C:3]([C:5]1[N:6]([NH2:10])[CH:7]=[N:8][CH:9]=1)=[O:4].[CH2:11]([N:18]1[CH2:22][CH:21]([C:23]([F:26])([F:25])[F:24])[CH:20]([C:27](O)=[O:28])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([NH:10][C:27]([CH:20]2[CH:21]([C:23]([F:25])([F:24])[F:26])[CH2:22][N:18]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:19]2)=[O:28])[CH:7]=[N:8][CH:9]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11665425Methyl 1-amino-1H-imidazole-5-carboxylateHCID 196913861-Benzyl-4-(trifluoromethyl)pyrrolidine-3-carboxylic acid

Produkt 1

HCID 89722227HCID 89722227, VerbindungAusbeute 85,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of compound 2 (2.0 g, 14.1 mmol), 1-Benzyl-4-trifluoromethyl-pyrrolidine-3-carboxylic acid (4.06 g, 14.9 mmol) and DIEA (10 mL, 42.5 mmol) in DMF (30 mL) was added HATU (8.1 g, 21.2 mmol). The resulting reaction mixture was stirred at r.t. overnight. The reaction was monitored by LC-MS. The reaction was quenched with water (100 mL) when it was complete. The aqueous solution was extracted with EtOAc (80 mL×3). The combined organic phase was washed with brine and concentrated to afford the crude product. The residue was purified by silica gel column (eluted with PE/EA=5:1 to 1:2) to afford compound 13 (4.8 g, 85.6% yield) as white oil. LC-MS: m/z 397 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 8.00 (br. s, 1H), 7.70 (s, 1H), 7.65 (s, 1H), 7.34˜7.28 (m, 5H), 3.81 (s, 3H), 3.78˜3.72 (m, 2H), 3.41˜3.38 (m, 1H), 3.30˜3.24 (m, 2H), 3.14˜3.12 (m, 1H), 2.71˜2.67 (m, 1H), 2.58˜2.53 (m, 1H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched with water (100 mL) when it
  3. extractionThe aqueous solution was extracted with EtOAc (80 mL×3)
  4. washThe combined organic phase was washed with brine
  5. concentrationconcentrated
  6. customto afford the crude product
  7. customThe residue was purified by silica gel column (eluted with PE/EA=5:1 to 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-0eb64468af20477ca88198566260bdf5
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434733B2

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