Triethylamine → HCID 11618423, Verbindung

HRID 2217773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2217773
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.[C:13]([C:17]1[S:21][C:20]([NH:22][C:23](=[O:29])[CH:24]([NH2:28])[CH2:25][CH2:26][CH3:27])=[N:19][N:18]=1)([CH3:16])([CH3:15])[CH3:14].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>C(Cl)Cl>[C:13]([C:17]1[S:21][C:20]([NH:22][C:23](=[O:29])[CH:24]([NH:28][C:10](=[O:12])[CH2:9][C:4]2[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=2)[CH2:25][CH2:26][CH3:27])=[N:19][N:18]=1)([CH3:15])([CH3:14])[CH3:16]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 1454243,5-Difluorophenylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 860331642-Amino-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide

Produkt 1

HCID 11618423HCID 11618423, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3,5-di-fluoro-phenyl acetic acid (51.6 mg, 0.3 mmol), 2-amino-pentanoic acid (5-tert-butyl-[1,3,4]thiadiazol-2-yl)-amide (88 mg, 0.3 mmol), HBOT (43 mg, 0.315 mmol), EDC HCl (69 mg, 0.36 mmol.) and triethylamine (0.17 ml) in methylene chloride was stirred at room temperature until product formation or disappearance of starting material. The mixture was quenched with water and extracted with methylene chloride. The organic layer was separated, washed with dilute HCl, brine, dried over sodium sulfate and the solvent was removed at reduced pressure to provide the title compound as a cude oil. The oil was purified by Shimadzu HPLC to provide the title compound as a white solid (56 mg), LC-MS M+1=411.2, 1H NMR(CDCL3) 8.7 (d,1H,NH), 6.73(m,2H), 6.6(m,1H), 4.7(m,1H), 3.5(Abq, 2H), 1.6-1.9(m,2H), 1.3-1.6(m,2H), 1.5(s,9H), 0.92(t,3H) ppm.

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with methylene chloride
  3. customThe organic layer was separated
  4. washwashed with dilute HCl, brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-181c8279f1564a35bcc0abc35c667ad2
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07408068B2

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