Hydrochloric Acid → 6-{2-{[4-(2-Cyclopropylaminoethoxy)benzyl]isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1434288

Reaktionsgleichung

Reaktionsgleichung von HRID 1434288
[OH:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([N:8]([CH:34]([CH3:36])[CH3:35])[C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[CH:17]2[CH2:26][CH2:25][C:24]3[CH:23]=[C:22]([O:27]C(=O)C(C)(C)C)[CH:21]=[CH:20][C:19]=3[CH2:18]2)=O)=[CH:4][CH:3]=1.Cl[CH2:40][C:41]([NH:43][CH:44]1[CH2:46][CH2:45]1)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].B.O1CCCC1.Cl.[OH-].[Na+]>O.O1CCCC1>[CH:44]1([NH:43][CH2:41][CH2:40][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][N:8]([CH:34]([CH3:36])[CH3:35])[C:9]3[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=3[CH:17]3[CH2:26][CH2:25][C:24]4[CH:23]=[C:22]([OH:27])[CH:21]=[CH:20][C:19]=4[CH2:18]3)=[CH:37][CH:38]=2)[CH2:46][CH2:45]1

Komponenten

10

Edukt 7

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 7357802-chloro-N-cyclopropylacetamideHCID 2723981Borane;tetrahydrofuranHCID 57933955Pivalic acid 6-{2-[(4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Produkt 1

HCID 579345306-{2-{[4-(2-Cyclopropylaminoethoxy)benzyl]isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olAusbeute 37,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of pivalic acid 6-{2-[(4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (25 mg), 2-chloro-N-cyclopropylacetamide (13 mg), cesium carbonate (32 mg), potassium iodide (5.0 mg) and tetrahydrofuran (2 ml) was stirred for 5 hours at 60° C. To the reaction solution was added dropwise borane-tetrahydrofuran complex (1.0 M solution in tetrahydrofuran) (0.49 ml), and the solution was stirred at 60° C. for one day and one night. The reaction solution was cooled to room temperature, concentrated hydrochloric acid (0.08 ml) was added thereto, the solution was stirred for 1.5 hours at 60° C., then an aqueous solution of 5N sodium hydroxide (1 ml) was added thereto, and the solution was stirred for 8 hours at 60° C. The reaction solution was diluted with water, then extracted with ethyl acetate. The organic layer was concentrated under a nitrogen stream; purified from a solution of the resulting residue in N,N-dimethylformamide by LC-MS, the title compound (9.0 mg) was obtained.

Aufarbeitung

  1. stirringthe solution was stirred at 60° C. for one day and one night
  2. temperatureThe reaction solution was cooled to room temperature
  3. stirringthe solution was stirred for 1.5 hours at 60° C.
  4. stirringthe solution was stirred for 8 hours at 60° C
  5. extractionextracted with ethyl acetate
  6. concentrationThe organic layer was concentrated under a nitrogen stream
  7. custompurified from a solution of the resulting residue in N,N-dimethylformamide by LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-9852d8dec263468eadf9219108ff44cb
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612114B2

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