1-Hydroxybenzotriazole → N-(4-cyclopropylphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxamide 2,2-dioxide

HRID 1622580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1622580
[N:1]1[S:2](=[O:15])(=[O:14])[CH2:3][CH2:4][N:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([OH:13])=O)[C:6]=12.[CH:16]1([C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)[CH2:18][CH2:17]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH:16]1([C:19]2[CH:25]=[CH:24][C:22]([NH:23][C:11]([C:7]3[C:6]4=[N:1][S:2](=[O:15])(=[O:14])[CH2:3][CH2:4][N:5]4[CH:10]=[CH:9][CH:8]=3)=[O:13])=[CH:21][CH:20]=2)[CH2:18][CH2:17]1

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 23846842,2-dioxo-3H,4H-2lambda6-pyrido[2,1-c][1,2,4]thiadiazine-9-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 122539274-Cyclopropylaniline

Produkt 1

HCID 66748364N-(4-cyclopropylphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxamide 2,2-dioxideAusbeute 74,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3,4-Dihydropyrido[2,1-c][1,2,4]thiadiazine-9-carboxylic acid 2,2-dioxide (150 mg) was dissolved in DMF (5 ml), 4-cyclopropylaniline (131 mg), HOBt (151 mg), EDCI HCl (189 mg) and DIEA (0.23 ml) were added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was suspended in ethyl acetate, and insoluble crystals were collected by filtration to give the title compound (168 mg) as pale-yellow crystals.

Aufarbeitung

  1. washwashed successively with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. filtrationinsoluble crystals were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-2673189f7428459d9aeaaeb3621b6e1f
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778934B2

Notizen zur Reaktion

Wird geladen…