Diisopropylethylamine → HCID 59487510, Verbindung

HRID 886728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 886728
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH:16][CH2:17][C:18]([CH2:24][NH2:25])([OH:23])[C:19]([F:22])([F:21])[F:20])=[O:15].[Br:26][C:27]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:28]=1[C:29](Cl)=[O:30].C(N(C(C)C)CC)(C)C>O1CCCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH:16][CH2:17][C:18]([CH2:24][NH:25][C:29]([C:28]1[C:32]([Cl:36])=[CH:33][CH:34]=[CH:35][C:27]=1[Br:26])=[O:30])([OH:23])[C:19]([F:22])([F:21])[F:20])=[O:15]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 27568702-Bromo-6-chlorobenzoyl chlorideHCID 594874945-amino-N-[2-(aminomethyl)-3,3,3-trifluoro-2-hydroxypropyl]-1-(4-fluorophenyl)-1H-pyrazole-4-carboxamide

Produkt 1

HCID 59487510HCID 59487510, VerbindungAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-amino-N-[2-(aminomethyl)-3,3,3-trifluoro-2-hydroxypropyl]-1-(4-fluorophenyl)-1H-pyrazole-4-carboxamide (250 mg, 0.69 mmol) in tetrahydrofuran (2 ml) was added 2-bromo-6-chlorobenzoyl chloride (192.7 mg, 0.76 mmol) followed by diisopropylethylamine (178 mg, 1.38 mmol). The reaction was left stirring under nitrogen overnight. LC-MS analysis showed the reaction was complete. The reaction mixture was concentrated in vacuo. The residue was redissolved in dichloromethane and washed with 2M hydrochloric acid followed by water. The organic layer was concentrated in vacuo to give the title compound (280 mg).

Aufarbeitung

  1. waitThe reaction was left
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washwashed with 2M hydrochloric acid
  5. concentrationThe organic layer was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4041a70785b64dbbb441fa0e4ac3cabe
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247377B2

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