Triethylamine → HCID 54137663, Verbindung

HRID 1740809

Reaktionsgleichung

Reaktionsgleichung von HRID 1740809
[CH3:1][S:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[N:8]([C:16](=[O:27])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24](O)=[O:25])[CH:19]=1)[CH2:7][CH2:6]2.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH3:41][N:42]([CH3:47])[CH2:43][CH2:44][NH:45][CH3:46]>ClCCl.C1COCC1.CN(C=O)C>[CH3:41][N:42]([CH3:47])[CH2:43][CH2:44][N:45]([CH3:46])[C:24]([C:20]1[CH:19]=[C:18]([NH:17][C:16]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([S:2][CH3:1])=[C:11]([C:12]([F:13])([F:15])[F:14])[CH:10]=3)[CH2:6][CH2:7]2)=[O:27])[CH:23]=[CH:22][CH:21]=1)=[O:25]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 180051075-Methylthio-6-trifluoromethyl-1-(3-carboxy Phenyl Carbamoyl)indoline

Produkt 1

HCID 54137663HCID 54137663, VerbindungAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The carboxylic acid from Example 12 (0.5 g, 1.25 mmol) in dichloromethane (10 ml) was treated with oxalyl chloride (0.3 ml, 3.4 mol) and DMF (catalytic). Solution was stirred for 1 h and evaporated to dryness. The residue in dry THF (5 ml) was added to a stirred solution of triethylamine (0.3 ml, 4 mmol) and N,N,N'-trimethylethylenediamine (0.5 ml, 4.5 mmol) in dry THF (10 ml). Following 3 hours at room temperature, the solution was partitioned (H2O/EtOAc). Drying and removal of the organic layers followed by recrystallisation (EtOAc/60°-80° petrol) afforded the title compound (0.5 g, 83%) as a white solid. M.pt. 140°-141° C.

Aufarbeitung

  1. customevaporated to dryness
  2. waitFollowing 3 hours at room temperature
  3. customthe solution was partitioned (H2O/EtOAc)
  4. customDrying
  5. customremoval of the organic layers
  6. customfollowed by recrystallisation (EtOAc/60°-80° petrol)

Quellen und Nachweise

ORD-Eintrag
ord-358a48d0a59041da99095b831ed2776a
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05972937

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