Oxalyl chloride → HCID 57732770, Verbindung

HRID 1806485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1806485
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.C(Cl)(=O)C(Cl)=O.[NH2:15][CH2:16][C:17]1[CH:18]=[C:19]([C:23]2[CH:24]=[C:25]3[C:29](=[C:30]([C:32]([NH2:34])=[O:33])[CH:31]=2)[NH:28][CH:27]=[C:26]3[CH:35]2[CH2:40][CH2:39][N:38]([S:41]([CH2:44][CH3:45])(=[O:43])=[O:42])[CH2:37][CH2:36]2)[CH:20]=[CH:21][CH:22]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.N1C=CC=CC=1.CN(C=O)C>[CH2:44]([S:41]([N:38]1[CH2:39][CH2:40][CH:35]([C:26]2[C:25]3[C:29](=[C:30]([C:32]([NH2:34])=[O:33])[CH:31]=[C:23]([C:19]4[CH:20]=[CH:21][CH:22]=[C:17]([CH2:16][NH:15][C:6]([CH:3]5[CH2:4][CH2:5][O:1][CH2:2]5)=[O:8])[CH:18]=4)[CH:24]=3)[NH:28][CH:27]=2)[CH2:36][CH2:37]1)(=[O:43])=[O:42])[CH3:45]

Komponenten

8

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 4661317(R)-Tetrahydro-3-furoic acidHCID 16038109HCID 16038109, Verbindung

Produkt 1

HCID 57732770HCID 57732770, VerbindungAusbeute 10,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tetrahydro-3-furancarboxylic acid (17 mg, 0.144 mmol) in DCM (2.0 mL) was added pyridine (3 drops) and oxalyl chloride (18 mg, 0.144 mmol). Reaction mixture was stirred overnight at room temperature. To the mixture was then added 5-[3-(aminomethyl)phenyl]-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (40 mg, 0.096 mmol) in DMF (1.0 mL) and DIEA (33 μL, 0.192 mmol). Reaction mixture was stirred at room temperature overnight. Reaction mixture was concentrated under nitrogen and purified by Gilson Preparatory HPLC to give 5.3 mg the title compound (10%).

Aufarbeitung

  1. customReaction mixture
  2. customReaction mixture
  3. stirringwas stirred at room temperature overnight
  4. customReaction mixture
  5. concentrationwas concentrated under nitrogen
  6. custompurified by Gilson Preparatory HPLC

Quellen und Nachweise

ORD-Eintrag
ord-fcd342de0dea4c0e97c422e62a3e0ef2
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354406B2

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