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p-Toluenesulfonic acid monohydrate → HCID 71811480, Verbindung

HRID 633358
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 633358
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:17][CH:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[C:11]([CH3:19])([CH3:18])[CH2:10]2)[C:5]([C:20]#[N:21])=[CH:4][N:3]=1.[CH:22]1([C:25]2[C:30]([N:31]3[CH:35]=[N:34][N:33]=[N:32]3)=[CH:29][C:28]([NH2:36])=[C:27]([F:37])[CH:26]=2)[CH2:24][CH2:23]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(C)C>[CH:22]1([C:25]2[C:30]([N:31]3[CH:35]=[N:34][N:33]=[N:32]3)=[CH:29][C:28]([NH:36][C:2]3[N:7]=[C:6]([NH:8][CH:9]4[CH2:17][CH:16]5[N:12]([CH2:13][CH2:14][CH2:15]5)[C:11]([CH3:19])([CH3:18])[CH2:10]4)[C:5]([C:20]#[N:21])=[CH:4][N:3]=3)=[C:27]([F:37])[CH:26]=2)[CH2:24][CH2:23]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58065786HCID 58065786, VerbindungHCID 86704469HCID 86704469, Verbindung

Produkt 1

HCID 71811480HCID 71811480, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of (±)-2-chloro-4-(octahydro-5,5-dimethylindolizin-7-ylamino)pyrimidine-5-carbonitrile (60 mg of 70% pure material from previous step), 4-cyclopropyl-2-fluoro-5-(1H-tetrazol-1-yl)benzeneamine (65 mg, 0.3 mmol; prepared according to U.S. patent application Ser. No. 13/188,222, filed Jul. 21, 2011, now U.S. patent application publication US2012/0022092) and para-toluenesulfonic acid monohydrate (37 mg, 0.2 mmol) in isopropyl alcohol (3 ml) were combined in a sealed vial, heated to 80° C. and stirred for 4 hours. After cooling, a precipitate emerged which was filtered. The filter cake was suspended in EtOAc (30 ml) and 1N NaOH (50 ml). The aqueous and organic layers were partitioned and the aqueous layer was extracted with EtOAc (2×25 ml). The combined organic extracts were dried (MgSO4), filtered and the solvent removed under vacuum to leave a solid. The solid was freeze-dried from MeCN/H2O to give the product (26 mg) as a solid.

Aufarbeitung

  1. customprepared
  2. temperatureAfter cooling
  3. filtrationwas filtered
  4. customThe aqueous and organic layers were partitioned
  5. extractionthe aqueous layer was extracted with EtOAc (2×25 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed under vacuum
  9. customto leave a solid
  10. dry with materialThe solid was freeze-dried from MeCN/H2O

Quellen und Nachweise

ORD-Eintrag
ord-41ec3ba69cb94465803777b664675d53
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09321763B2

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