Triethylamine → 4-{5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid

HRID 448930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448930
C([O:5][C:6]([CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:20]=[C:19]([Cl:21])[C:18]([C:22]2[CH:23]=[N:24][C:25]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:27]=2[C:28]#[N:29])=[CH:17][C:13]=1[C:14]([OH:16])=O)=[O:7])(C)(C)C.[CH3:34][O:35][C:36]1[CH:43]=[CH:42][CH:41]=[CH:40][C:37]=1[NH:38][CH3:39].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>ClCCl.CN(C=O)C>[Cl:21][C:19]1[C:18]([C:22]2[CH:23]=[N:24][C:25]([C:30]([F:32])([F:31])[F:33])=[CH:26][C:27]=2[C:28]#[N:29])=[CH:17][C:13]([C:14](=[O:16])[N:38]([C:37]2[CH:40]=[CH:41][CH:42]=[CH:43][C:36]=2[O:35][CH3:34])[CH3:39])=[C:12]([CH:20]=1)[O:11][CH2:10][CH2:9][CH2:8][C:6]([OH:5])=[O:7]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 27595792-Methoxy-N-methylanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 686028022-(3-Tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid

Produkt 1

HCID 251589894-{5-Chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid (30 mg, 0.06 mmol), 2-methoxy-N-methylaniline (9.4 mg, 0.07 mmol), triethylamine (12.5 mg, 0.12 mmol) and 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 35 mg, 0.09 mL) in dichloromethane (1 mL) containing DMF (0.1 mL) was stirred at rt for 16 hrs. The mixture was then partitioned in water and dichloromethane. The organic layer was washed with water, dried and concentrated to yield a crude 4-{5-chloro-4-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-2-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenoxy}-butyric acid t-butyl ester.

Aufarbeitung

  1. customThe mixture was then partitioned in water
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0b3ae6592920410b94269643d05493af
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481738B2

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