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Dimethylamine → N-((1R,2S)-1-(1-(4-((dimethylamino)methyl)phenyl)-1H-indazol-5-yloxy)-1-phenylpropan-2-yl)-2,2,2-trifluoroacetamide

HRID 13179
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 13179
[F:1][C:2]([F:34])([F:33])[C:3]([NH:5][C@@H:6]([CH3:32])[C@H:7]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30]O)=[CH:26][CH:25]=1)[N:19]=[CH:18]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].[CH2:35]([N:37](CC)[CH2:38]C)C.CS(Cl)(=O)=O.CNC>[Cl-].[Na+].O.ClCCl>[CH3:35][N:37]([CH2:30][C:27]1[CH:26]=[CH:25][C:24]([N:20]2[C:21]3[C:17](=[CH:16][C:15]([O:14][C@H:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C@@H:6]([NH:5][C:3](=[O:4])[C:2]([F:34])([F:33])[F:1])[CH3:32])=[CH:23][CH:22]=3)[CH:18]=[N:19]2)=[CH:29][CH:28]=1)[CH3:38]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59339791HCID 59339791, Verbindung

Produkt 1

HCID 59339629N-((1R,2S)-1-(1-(4-((dimethylamino)methyl)phenyl)-1H-indazol-5-yloxy)-1-phenylpropan-2-yl)-2,2,2-trifluoroacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a stirred, ice-cooled suspension of 2,2,2-trifluoro-N-((1R,2S)-1-(1-(4-(hydroxymethyl)phenyl)-1H-indazol-5-yloxy)-1-phenylpropan-2-yl)acetamide (141, 118 mg, 0.25 mmol) and triethylamine (0.35 mL, 2.5 mmol) was added methanesulfonyl chloride (140 μL, 1.8 mmol). After stirring for 50 min at 0° C. brine and dichloromethane (10 mL) were added. The mixture was washed with aqueous KHSO4 (1M) and sat. aqueous NaHCO3. To the organic phase was added dimethylamine (0.75 mL, 11.3 mmol). The mixture was stirred at ambient temperature for 40 min and was then evaporated. Preparative HPLC (Kromasil C-18, 2.5×20 cm, 30-90% CH3CN in water/40 min (0.1% TfA) afforded slightly impure title compound as a TfA-salt. The material was dissolved in MeOH and absorbed on a plug of acidic ion exchange resin (SCX, 5 g, pre-washed with MeOH). Eluting subsequently with MeOH and methanolic ammonia (2M) gave somewhat impure title compound. Purification by preparative HPLC on an XBridge C-18 column using a gradient of 50-90% acetonitrile in water containing 0.1% aqueous ammonia (28%). afforded pure N-((1R,2S)-1-(1-(4-((dimethylamino)methyl)phenyl)-1H-indazol-5-yloxy)-1-phenylpropan-2-yl)-2,2,2-trifluoroacetamide (77 mg, 61%).

Aufarbeitung

  1. temperatureTo a stirred, ice-cooled
  2. additionwere added
  3. washThe mixture was washed with aqueous KHSO4 (1M) and sat. aqueous NaHCO3
  4. customwas then evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e60db255636348b88ba5b56379604c90
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728030B2

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