Hydrochloric Acid → HCID 178509613, Verbindung

HRID 578963

Reaktionsgleichung

Reaktionsgleichung von HRID 578963
[CH:1]1[CH:2]=[CH:3][C:4]2N(O)N=[N:7][C:5]=2C=1.CCN=C=NCCCN(C)C.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[N:32][N:33]([C:36]3[CH:44]=[CH:43][C:39]([C:40]([OH:42])=O)=[CH:38][N:37]=3)[C:34]=2[OH:35])=[CH:26][CH:25]=1)#[N:23].CCN(C(C)C)C(C)C.C1(CCN)CC1.Cl>CN(C=O)C.CO.O>[C:22]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[N:32][N:33]([C:36]3[CH:44]=[CH:43][C:39]([C:40]([NH:7][CH2:5][CH2:4][CH:3]4[CH2:2][CH2:1]4)=[O:42])=[CH:38][N:37]=3)[C:34]=2[OH:35])=[CH:26][CH:25]=1)#[N:23]

Komponenten

10

Edukt 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10240761CyclopropaneethanamineHCID 178509615HCID 178509615, Verbindung

Produkt 1

HCID 178509613HCID 178509613, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Combined HOBT (66.2 mg, 0.490 mmol) and EDCI (94 mg, 0.490 mmol), a solution 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (100 mg, 0.327 mmol, in DMF (1 mL)) and Hunig's base (169 mg, 1.306 mmol) in DMF (1 mL). Then 2-cyclopropylethanamine (41.7 mg, 0.490 mmol) was added and the reaction was stirred at ambient temperature for 14 h. The reaction mixture was diluted with MeOH (2 mL) and water (3 mL) and acidified to pH 4 using 1 N HCl to give a solid which were collected by filtration and recrystallized from MeOH to give the title compound as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.01-0.14 (m, 2 H) 0.35-0.49 (m, 2 H) 0.68-0.81 (m, 1 H) 1.46 (q, J=7.07 Hz, 2 H) 3.27-3.43 (m, 2 H) 7.79 (d, J=8.59 Hz, 2 H) 8.14 (d, J=6.32 Hz, 2 H) 8.34-8.79 (m, 4 H) 8.85-8.97 (m, 1 H) 13.53 (br. s., 1 H). MS m/z [M+H]+ 374.2.

Aufarbeitung

  1. customto give a solid which
  2. filtrationwere collected by filtration
  3. customrecrystallized from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-ad2f1f5be5f14e0683fc5bf14ac7f3c7
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040522B2

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