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Trimethyl orthoformate → HCID 72948500, Verbindung

HRID 921640
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 921640
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[CH:6][C:5]([C:15]#[N:16])=[CH:4][C:3]=1[NH:17][C:18]1[N:23]=[C:22]([N:24]([CH:34]2[CH2:36][CH2:35]2)CC2C=CC(OC)=CC=2)[C:21]2=[N:37][CH:38]=[C:39]([C:40]#[N:41])[N:20]2[N:19]=1.[F:42][C:43]1([F:48])[CH2:46][CH:45]([NH2:47])[CH2:44]1.C(OC)(OC)OC.C([BH3-])#N.[Na+]>CO.O1CCCC1.O>[Cl:1][C:2]1[C:7]([N:8]2[CH2:9][CH2:10][CH:11]([NH:47][CH:45]3[CH2:46][C:43]([F:48])([F:42])[CH2:44]3)[CH2:12][CH2:13]2)=[CH:6][C:5]([C:15]#[N:16])=[CH:4][C:3]=1[NH:17][C:18]1[N:23]=[C:22]([NH:24][CH:34]2[CH2:35][CH2:36]2)[C:21]2=[N:37][CH:38]=[C:39]([C:40]#[N:41])[N:20]2[N:19]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 9005Trimethyl orthoformateHCID 5003444Sodium cyanoborohydrideHCID 225009513,3-Difluorocyclobutan-1-amineHCID 86708485HCID 86708485, Verbindung2×

Produkt 1

HCID 72948500HCID 72948500, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887
Methanol
Lösungsmittel
2×
HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a vial charged with 2-((2-chloro-5-cyano-3-(4-oxopiperidin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Intermediate 13) (30 mg, 0.053 mmol) and 3,3-difluorocyclobutanamine (6.79 mg, 0.063 mmol) in methanol (132 μl) and tetrahydrofuran (132 μl) was added trimethyl orthoformate (58.4 μl, 0.528 mmol). The reaction mixture was stirred at room temperature. Sodium cyanoborohydride (6.64 mg, 0.106 mmol) was added and the reaction mixture was stirred at room temperature 6 h. The reaction mixture was diluted with water and methanol and filtered. The solid was taken up in DMF and partitioned between water and ethyl acetate. The aqueous layer was washed with ethyl acetate (3×). The combined organics were washed with 10% lithium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude material was taken forward as is.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature 6 h
  2. filtrationfiltered
  3. custompartitioned between water and ethyl acetate
  4. washThe aqueous layer was washed with ethyl acetate (3×)
  5. washThe combined organics were washed with 10% lithium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6be7fbc5d481466fa23d04a7b70160d5
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09273057B2

Notizen zur Reaktion

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