Triethylamine → 3-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-phenylamino)-cyclobutanecarboxylic acid

HRID 1177638

Reaktionsgleichung

Reaktionsgleichung von HRID 1177638
[F:1][C:2]1[CH:3]=[C:4]([NH2:26])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.O=[C:28]1[CH2:31][CH:30]([C:32]([OH:34])=[O:33])[CH2:29]1.C(N(CC)CC)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:26][CH:28]2[CH2:31][CH:30]([C:32]([OH:34])=[O:33])[CH2:29]2)[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][CH2:19]1)[N:11]=2

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 49133583-Oxocyclobutane-1-carboxylic acidHCID 574030523-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzenamine

Produkt 1

HCID 591748373-(3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-phenylamino)-cyclobutanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzenamine (183 mg, 0.506 mmol) and 3-oxocyclobutanecarboxylic acid (63.5 mg, 0.557 mmol) in DCM (2.5 mL) and triethylamine (212 μl, 1.519 mmol) was added titanium(IV) chloride in DCM (0.759 ml, 0.759 mmol) at ambient temperature. The reaction mixture was concentrated, suspended in water, filtered, washed with water, and dried in a vacuum oven to give 3-((3-fluoro-4-(5-(1-phenyl-cyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)phenyl)amino)cyclobutanecarboxylic acid as yellow solid. MS (ESI) m/z: Calculated: 459.1; Observed: 460.4 (M++H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered
  3. washwashed with water
  4. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-f57d659a4822441abf69d07773d73999
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842685B2

Verknüpfte Notizen

Wird geladen…