5-Amino-1-methyl-1H-pyrazole-4-carbonitrile → 4-Methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid (4-cyano-2-methyl-2H-pyrazol-3-yl)amide

HRID 427301

Reaktionsgleichung

Reaktionsgleichung von HRID 427301
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]#[N:9].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[N+](C1C=CC([O:29][C:30]([C:32]2[C:40]3[S:39][C:38]([C:41]([F:44])([F:43])[F:42])=[N:37][C:36]=3[C:35]([O:45][CH3:46])=[CH:34][CH:33]=2)=O)=CC=1)([O-])=O>CN(C)C=O.O1CCCC1>[C:8]([C:3]1[CH:4]=[N:5][N:6]([CH3:7])[C:2]=1[NH:1][C:30]([C:32]1[C:40]2[S:39][C:38]([C:41]([F:44])([F:43])[F:42])=[N:37][C:36]=2[C:35]([O:45][CH3:46])=[CH:34][CH:33]=1)=[O:29])#[N:9]

Komponenten

6

Edukt 3

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 2724254Sodium bis(trimethylsilyl)amideHCID 69689660Methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid 4-nitrophenyl ester

Produkt 1

HCID 101344224-Methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid (4-cyano-2-methyl-2H-pyrazol-3-yl)amideAusbeute 34,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5-amino-1-methyl-1H-pyrazole-4-carbonitrile (93 mg) in dimethyl formamide (10 ml) was treated with a solution of sodium hexamethyldisilazide in tetrahydrofuran (0.76 ml, 1.0M). After three minutes the mixture was treated with 4-methoxy-2-trifluoromethylbenzothiazole-7-carboxylic acid 4-nitrophenyl ester (150 mg) and the reaction stirred at room temperature for 2 hours. The solvent was removed in vacuo. Purification by flash chromatography (eluent ethyl acetate) to yield the title compound as an off-white solid (50 mg). TLC Rf 0.48 (ethyl acetate); MS found M+1 382.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customPurification by flash chromatography (eluent ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e5d06c294e4242d0a0167a947c4a05cb
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313116B1

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