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Sodium Bicarbonate → HCID 67443027, Verbindung

HRID 1400925
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1400925
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7]C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.[CH:15]1([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][N:32]=[C:31]4[CH:35]=[C:36]([C:38]5[CH:43]=[CH:42][C:41]([CH:44]=O)=[CH:40][N:39]=5)[S:37][C:30]=34)=[C:24]([F:46])[CH:23]=2)=[O:20])[CH2:17][CH2:16]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>CN1C(=O)CCC1.CC(O)=O>[NH2:7][CH:4]1[CH2:3][CH2:2][N:1]([CH2:44][C:41]2[CH:42]=[CH:43][C:38]([C:36]3[S:37][C:30]4[C:31](=[N:32][CH:33]=[CH:34][C:29]=4[O:28][C:25]4[CH:26]=[CH:27][C:22]([NH:21][C:19]([NH:18][CH:15]5[CH2:16][CH2:17]5)=[O:20])=[CH:23][C:24]=4[F:46])[CH:35]=3)=[N:39][CH:40]=2)[CH2:6][CH2:5]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 582365791-Cyclopropyl-3-(3-fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

Produkt 1

HCID 67443027HCID 67443027, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 176Acetic AcidLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

tert-Butyl piperidin-4-ylcarbamate (1.34 g, 6.69 mmol) was added to a solution of the aldehyde 47 (2.0 g, 4.46 mmol) in a mixture of NMP (20 mL) and glacial AcOH (0.250 mL). The reaction mixture was stirred for 30 min. NaBH(OAc)3 was then added and the reaction mixture was stirred for an additional 2.5 hours. The reaction mixture was then poured into a saturated aqueous NaHCO3 solution. A precipitate was formed which was collected by filtration, washed with water and air-dried. The crude material was purified by column chromatography using a 5 to 20% gradient of MeOH in EtOAc as eluent to afford the title compound 343 (1.45 g, 51.4% yield). MS (m/z): 633.6 (M+1)+.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for an additional 2.5 hours
  2. customA precipitate was formed which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customair-dried
  6. customThe crude material was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-99465bcc27c646c8afa8e1c926354fde
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906852B2

Notizen zur Reaktion

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