Triethylamine → 4-bromo-N-[(cis)-2-hydroxycyclohexyl]quinoline-2-carboxamide

HRID 1497321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497321
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([OH:14])=O)[CH:3]=1.[Cl-].[OH:16][C@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]1[NH3+:23].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([NH:23][C@@H:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C@@H:17]2[OH:16])=[O:14])[CH:3]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11263589[(1R,2S)-2-hydroxycyclohexyl]azanium;chlorideHCID 155308124-Bromoquinoline-2-carboxylic acid

Produkt 1

HCID 673239414-bromo-N-[(cis)-2-hydroxycyclohexyl]quinoline-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of the 4-bromoquinoline-2-carboxylic acid (A3) (0.10 g, 0.40 mmol) in 2.0 mL, CH2Cl2 was added (cis)-2-hydroxycyclohexanaminium chloride (0.12 g, 0.80 mmol), BOP reagent (0.35 g, 0.80 mmol), and triethylamine (0.16 mL, 1.2 mmol). The reaction mixture was stirred at room temperature for 16 h, diluted with CH2Cl2, washed with water, dried over sodium sulfate, filtered, and concentrated. The resultant residue subjected to silica gel chromatography eluting with 0-60% ethyl acetate in hexanes to afford 4-bromo-N-[(cis)-2-hydroxycyclohexyl]quinoline-2-carboxamide (I1) that gave a mass ion (ES+) of 349.2 (79Br) for M+H+.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluting with 0-60% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-04f8c1f59127471e920f94450027aa78
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199939B2

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