Acetic Acid → {2-Amino-6-[6-(tert-butylaminomethyl)benzo-1,3-dioxol-5-yl]quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone

HRID 1631122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631122
[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[C:24]([CH:32]=O)=[CH:25][C:26]4[O:30][CH2:29][O:28][C:27]=4[CH:31]=3)[CH:8]=2)[N:3]=1.[C:34]([NH2:38])([CH3:37])([CH3:36])[CH3:35].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.O1CCCC1.O>[NH2:1][C:2]1[N:11]=[C:10]([C:12]([N:14]2[CH2:15][C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:22]2)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]3[C:24]([CH2:32][NH:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:25][C:26]4[O:30][CH2:29][O:28][C:27]=4[CH:31]=3)[CH:8]=2)[N:3]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 6385Tert-ButylamineHCID 5049666Sodium triacetoxyborohydrideHCID 871741096-[2-Amino-4-(isoindoline-2-carbonyl)quinazolin-6-yl]-1,3-benzodioxole-5-carbaldehyde

Produkt 1

HCID 56943542{2-Amino-6-[6-(tert-butylaminomethyl)benzo-1,3-dioxol-5-yl]quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

100 mg of 6-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]-benzo-1,3-dioxole-5-carbaldehyde are dissolved in 2 ml of 1,2-dichloroethane and 2 ml of tetrahydrofuran. 30 μl of tert-butylamine and 13 μl of glacial acetic acid are added, and the mixture is stirred at 60° C. for 6 h. After cooling to 25° C., 102 mg of sodium triacetoxyborohydride are added and stirred at 25° C. for a further 12 h. The mixture is poured into water, extracted three times with dichloromethane, and the combined organic phases are dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness and purified by chromatography (reversed phase HPLC).

Aufarbeitung

  1. temperatureAfter cooling to 25° C.
  2. stirringstirred at 25° C. for a further 12 h
  3. extractionextracted three times with dichloromethane
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe filtrate is evaporated to dryness
  7. custompurified by chromatography (reversed phase HPLC)

Quellen und Nachweise

ORD-Eintrag
ord-3e160cd1a759401296679244717946a4
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791129B2

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