Sodium hydride → HCID 178509393, Verbindung

HRID 1518289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518289
[NH2:1][C:2]1[N:6](C(OC(C)(C)C)=O)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:3]=1[C:21]#[N:22].[H-].[Na+].[S:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[C:26]1[NH:34][C:35]([C:37]1[CH:38]=[CH:39][CH:40]=[C:41]2[C:46]=1[CH2:45][N:44]([C:47]1[S:48][C:49]([CH2:57][CH2:58][CH2:59]I)=[C:50]([C:52]([O:54]CC)=[O:53])[N:51]=1)[CH2:43][CH2:42]2)=[O:36]>CN(C=O)C.Cl.CS(C)=O.CO>[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:59][CH2:58][CH2:57][C:49]3[S:48][C:47]([N:44]4[CH2:43][CH2:42][C:41]5[C:46](=[C:37]([C:35](=[O:36])[NH:34][C:26]6[S:25][C:29]7[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=7[N:27]=6)[CH:38]=[CH:39][CH:40]=5)[CH2:45]4)=[N:51][C:50]=3[C:52]([OH:54])=[O:53])=[CH:18][CH:19]=2)[C:3]=1[C:21]#[N:22]

Komponenten

8

Edukt 3

HCID 24758Sodium hydrideHCID 59447467ethyl 2-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-5-(3-iodopropyl)thiazole-4-carboxylateHCID 136027725tert-butyl 5-amino-4-cyano-3-(4-hydroxyphenyl)-1H-pyrazole-1-carboxylate

Produkt 1

HCID 178509393HCID 178509393, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 679Dimethyl SulfoxideLösungsmittelHCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To compound 31F (0.132 g, 0.44 mmol) in DMF (4 mL) was added 60% sodium hydride (0.048 g, 1.2 mmol) at 0° C. The solution was stirred for 10 minutes. To this solution was added compound 2C. The solution was stirred at rt for 2 hours. The solution was diluted with conc. HCl (0.5 mL), and heated at 60° C. for 30 minutes. The mixture was diluted with DMSO (5 mL) and MeOH (9 mL). The solid was filtered off. The filtrate was then purified by Prep HPLC to provide 12 mg of the desired product: 1H NMR (DMSO-d6): δ 8.03 (d, J=7.98 Hz, 1H), 7.79 (d, J=7.98 Hz, 1H), 7.67-7.71 (m, 4H), 7.33-7.49 (m, 5H), 7.00 (d, J=8.59 Hz, 2H), 4.84 (s, 2H), 4.03 (t, J=5.98 Hz, 2H), 3.71-3.74 (m, 2H), 3.17-3.20 (m, 2H), 3.01-3.05 (m, 2H), 2.02 (m, 2H). MS (ESI(+)): 677 (M+H).

Aufarbeitung

  1. stirringThe solution was stirred at rt for 2 hours
  2. filtrationThe solid was filtered off
  3. customThe filtrate was then purified by Prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9b5d6183273046099c1cc16e837531f2
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232273B2

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