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Dimethylformamide → HCID 76687048, Verbindung

HRID 2178181
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2178181
CN(C=O)C.FC(F)(F)C(O)=O.[F:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([NH:21][C:22]2[N:27]=[C:26]([NH:28][C:29]3[CH:30]=[CH:31][C:32]4[O:36][C:35](=[O:37])[NH:34][C:33]=4[CH:38]=3)[C:25]([CH3:39])=[CH:24][N:23]=2)=[CH:16][C:15]=1[O:40][CH3:41].C([O-])([O-])=O.[Cs+].[Cs+].[P:48]([O:60][CH2:61]Cl)([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49]>O>[P:48]([O:60][CH2:61][N:34]1[C:33]2[CH:38]=[C:29]([NH:28][C:26]3[C:25]([CH3:39])=[CH:24][N:23]=[C:22]([NH:21][C:17]4[CH:18]=[C:19]([CH3:20])[C:14]([F:13])=[C:15]([O:40][CH3:41])[CH:16]=4)[N:27]=3)[CH:30]=[CH:31][C:32]=2[O:36][C:35]1=[O:37])([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])([O:55][C:56]([CH3:57])([CH3:58])[CH3:59])=[O:49]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 11701630Di-tert-butyl (chloromethyl) phosphate2×HCID 66713692HCID 66713692, Verbindung

Produkt 1

HCID 76687048HCID 76687048, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel
2×

Versuchsvorschrift

With reference to Scheme (XI), A DMF (300 mL) suspension of 5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)benzo[d]oxazol-2(3H)-one trifluoroacetate (prepared as described in Example 3) (40.38 g, 79 mmol) and Cs2CO3 (78.3 g, 238 mmol) was stirred at rt under Nitrogen atmosphere, after 2.5 h, di-tert-butyl chloromethyl phosphate (26.6 g, 103 mmol) was added and stirring was continued at room temperature. After 49 h, by LC-MS, the reaction was >90% complete (note: due to relatively poor quality of alkylating agent of this batch, additional ˜7 g of di-tert-butyl chloromethyl phosphate was added). With stirring, the reaction mixture was poured into 1.2 L of H2O, ppt formed and was a bit lumpy, additional 500 mL of H2O was added to ensure the formation of non-sticky solid. Precipitate was collected by filtration, washed with water, and was further dried under high vac. Compound di-tert-butyl (5-(2-(4-fluoro-3-methoxy-5-methylphenylamino)-5-methylpyrimidin-4-ylamino)-2-oxobenzo[d]oxazol-3(2H)-yl)methyl phosphate was obtained as a light brown solid and was used directly in the next reaction.

Aufarbeitung

  1. stirringstirring
  2. customwas continued at room temperature
  3. waitAfter 49 h
  4. additionwas added)
  5. stirringWith stirring
  6. customformed
  7. additionwas added
  8. filtrationPrecipitate was collected by filtration
  9. washwashed with water
  10. customwas further dried under high vac

Quellen und Nachweise

ORD-Eintrag
ord-b58f27cc10754ee38c3484f0bbc8469a
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09067925B2

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