Dichloromethane → HCID 59023003, Verbindung

HRID 1921767Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921767
C(OC(=O)[N:7]([C:30]1[CH:35]=[CH:34][C:33]([N:36]2[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]2)=[CH:32][CH:31]=1)[C:8]1[C:9]2[N:10]([CH:27]=[CH:28][N:29]=2)[C:11]([Sn](CCCC)(CCCC)CCCC)=[CH:12][N:13]=1)(C)(C)C.Br[C:45]1[O:49][C:48]([C:50]([NH2:52])=[O:51])=[CH:47][CH:46]=1.C(Cl)Cl>C1COCC1.C(O)(C(F)(F)F)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH3:7].[CH3:42][N:39]1[CH2:40][CH2:41][N:36]([C:33]2[CH:34]=[CH:35][C:30]([NH:7][C:8]3[C:9]4[N:10]([CH:27]=[CH:28][N:29]=4)[C:11]([C:45]4[O:49][C:48]([C:50]([NH2:52])=[O:51])=[CH:47][CH:46]=4)=[CH:12][N:13]=3)=[CH:31][CH:32]=2)[CH2:37][CH2:38]1

Komponenten

8

Edukt 3

HCID 6344DichloromethaneHCID 2335815-Bromofuran-2-carboxamideHCID 67117498HCID 67117498, Verbindung

Produkt 2

HCID 222AmmoniaHCID 59023003HCID 59023003, VerbindungAusbeute 21,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6422Trifluoroacetic acidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In the same way as described for Compound 145, step 2 using [4-(4-methyl-piperazin-1-yl)-phenyl]-(5-tributylstannanyl-imidazo[1,2-a]pyrazin-8-yl)-carbamic acid tert-butyl ester (0.068 g, 0.162 mmol) in THF (3 mL), 5-bromo-furan-2-carboxylic acid amide (0.061 g, 0.324 mmol) and Pd(PPh3)4 (0.009 g, 0.008 mmol). The crude reaction mixture is stirred in (1:1) TFA:DCM (2 mL) for 2 hours at room temperature. Purification of the crude by silica gel column chromatography, eluting with DCM followed by 97:3 DCM:NH3 (7M in MeOH), affords the title compound (7.4 mg, 11%). LCMS: Rt 1.81 min (99%) m/z (APCI) 418 (M+H)+; 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.26 (3H, s), 2.49-2.53 (4H, m), 3.14 (4H, m), 6.97 (2H, d), 7.28 (1H, d, 7.34 (1H, d), 7.58 (1H, br s), 7.82 (1H, s), 7.90 (2H, d), 8.02 (1H, br s), 8.15 (1H, s), 8.48 (1H, s), 9.62 (1H, s).

Aufarbeitung

  1. customThe crude reaction mixture
  2. customPurification of the crude by silica gel column chromatography
  3. washeluting with DCM

Quellen und Nachweise

ORD-Eintrag
ord-ba7070c41f54496c992c3c2f5ceba654
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173656B2

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