Water → HCID 89620489, Verbindung

HRID 1499994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1499994
[Cl:1][C:2]1[C:10]([C:11]2[CH2:15][CH:14]([CH2:16][C:17]#[N:18])[O:13][N:12]=2)=[C:9]([S:19]([CH2:22][CH3:23])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C([NH:27][C:28]1[N:32]([CH3:33])[N:31]=[N:30][N:29]=1)C=C.C(Cl)(=O)C(Cl)=O.O>N1C=CC=CC=1.ClC(Cl)C>[Cl:1][C:2]1[C:10]([C:11]2[CH2:15][CH:14]([CH2:16][C:17]#[N:18])[O:13][N:12]=2)=[C:9]([S:19]([CH2:22][CH3:23])(=[O:20])=[O:21])[CH:8]=[CH:7][C:3]=1[C:4]([NH:27][C:28]1[N:32]([CH3:33])[N:31]=[N:30][N:29]=1)=[O:5]

Komponenten

7

Edukt 4

HCID 962WaterHCID 65578Oxalyl chlorideHCID 54595140HCID 54595140, VerbindungHCID 67041496HCID 67041496, Verbindung

Produkt 1

HCID 89620489HCID 89620489, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

178 mg (0.5 mmol) of 2-chloro-3-[5-(cyanomethyl)-4,5-dihydro-1,2-oxazol-3-yl]-4-(ethylsulfonyl)benzoic acid and 90 mg (0.65 mmol) of N-allyl-1-methyl-1H-tetrazol-5-amine are stirred in 3 ml of pyridine at room temperature (RT) for 1 h, and then a solution of 86 mg (0.675 mmol) of oxalyl chloride in 2 ml of dichloroethane is added. Subsequently, the mixture is stirred at 75° C. for 4 h. After cooling to RT, 0.5 ml of water is added. Then the mixture is stirred at RT for 30 min. The reaction solution is filtered and concentrated. The residue is purified by means of preparative HPLC (acetonitrile/water). Yield: 19 mg (8%).

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. stirringThen the mixture is stirred at RT for 30 min
  3. filtrationThe reaction solution is filtered
  4. concentrationconcentrated
  5. customThe residue is purified by means of preparative HPLC (acetonitrile/water)

Quellen und Nachweise

ORD-Eintrag
ord-89b8ed821e2b408fbdc7fc12a3897719
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09204650B2

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