Triethylamine → 3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-[(6-p-tolyl-pyridine-2-carbonyl)-amino]-propionic acid

HRID 405019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 405019
C([O:3][C:4](=[O:49])[CH:5]([NH:33][C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)[N:37]=1)=[O:35])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[C:9]([F:32])[CH:8]=1)C.C1(C)C=CC(C2N=C(C(O)=O)C=CC=2)=CC=1.C(OC(=O)C(N)CC1C=CC(C2N=C(C3C=CC(NC(OC(C)(C)C)=O)=CC=3)ON=2)=C(F)C=1)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.C([O-])(O)=O.[Na+]>ClCCl>[C:28]([O:27][C:25]([NH:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]2[O:15][N:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([CH2:6][CH:5]([NH:33][C:34]([C:36]4[CH:41]=[CH:40][CH:39]=[C:38]([C:42]5[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=5)[N:37]=4)=[O:35])[C:4]([OH:49])=[O:3])=[CH:8][C:9]=3[F:32])[N:17]=2)=[CH:23][CH:22]=1)=[O:26])([CH3:31])([CH3:30])[CH3:29]

Komponenten

8

Edukt 6

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 127849986-(4-Methylphenyl)pyridine-2-carboxylic acidHCID 66630730Ethyl 2-amino-3-(4-(5-(4-((tert-butoxycarbonyl)amino)phenyl)-1,2,4-oxadiazol-3-yl)-3-fluorophenyl)propanoateHCID 666313083-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluorophenyl}-2-[(6-p-tolyl-pyridine-2-carbonyl)-amino]-propionic acid ethyl ester

Produkt 1

HCID 533718963-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluoro-phenyl}-2-[(6-p-tolyl-pyridine-2-carbonyl)-amino]-propionic acidAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-{4-[5-(4-tert-Butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluorophenyl}-2-[(6-p-tolyl-pyridine-2-carbonyl)-amino]-propionic acid ethyl ester. A mixture of 6-p-tolyl-pyridine-2-carboxylic acid (47 mg, 0.1 mmol), 2-amino-3-{4-[5-(4-tert-butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-3-fluorophenyl}propionic acid ethyl ester (30 mg), HATU (46 mg, 0.12 mmol), and Et3N (15 mg, 0.15 mmol) in dichloromethane (5 mL) was stirred at room temperature overnight. TLC showed the reaction was completed. Saturated aqueous NaHCO3 (20 mL) was added to the mixture, and organic and aqueous layers were separated. The aqueous portion was extracted with dichloromethane (2×50 mL). The combined organic layers were washed sequentially with aq. HCl (1N, 2×50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated to give the title compound (53 mg, 80% yield).

Aufarbeitung

  1. customorganic and aqueous layers were separated
  2. extractionThe aqueous portion was extracted with dichloromethane (2×50 mL)
  3. washThe combined organic layers were washed sequentially with aq. HCl (1N, 2×50 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-24e28333b32043bcb2ec2a8d72d94ada
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748412B2

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