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Trifluoroacetic acid → 4-[(azetidin-3-ylmethyl)amino]-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-2-(tetrahydro-2H-pyran-4-ylamino)benzamide

HRID 1186619
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1186619
[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[C:45]([F:47])[CH:46]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([NH:24][CH2:25][CH:26]2[CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]2)=[CH:20][C:19]=1[NH:37][CH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)=[O:17].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:28]1[CH2:27][CH:26]([CH2:25][NH:24][C:21]2[CH:22]=[CH:23][C:18]([C:16]([NH:15][C:9]3[C:8]4[C:12](=[CH:13][CH:14]=[C:6]([CH2:5][C:4]5[CH:44]=[C:45]([F:47])[CH:46]=[C:2]([F:1])[CH:3]=5)[CH:7]=4)[NH:11][N:10]=3)=[O:17])=[C:19]([NH:37][CH:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)[CH:20]=2)[CH2:29]1
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 68671777tert-butyl 3-({[4-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-3-(tetrahydro-2H-pyran-4-ylamino)phenyl]amino}methyl)azetidine-1-carboxylate

Produkt 1

HCID 595773424-[(azetidin-3-ylmethyl)amino]-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-2-(tetrahydro-2H-pyran-4-ylamino)benzamideAusbeute 24,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

tert-butyl 3-({[4-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-3-(tetrahydro-2H-pyran-4-ylamino)phenyl]amino}methyl)azetidine-1-carboxylate (738 mg, 1.1 mmol) was dissolved in DCM (12 mL) and TFA (3 mL) was added. The resulting reaction solution was stirred for 3 hours at room temperature. The mixture was diluted with DCM and extracted with 10% acqueous NH3. Acqueous phase was extracted several time with DCM. Collected organic phases were washed with brine, dried over sodium sulfate and evaporated to dryness. Column chromatography purification on silica gel using dichloromethane/methanol/NH3 5N in MeOH 70:30:1 as the eluant, afforded 150 mg of the title compound.

Aufarbeitung

  1. customThe resulting reaction solution
  2. extractionextracted with 10% acqueous NH3
  3. extractionAcqueous phase was extracted several time with DCM
  4. washCollected organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customColumn chromatography purification on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-06c5ab97573e44ca89ced920574d53bf
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673893B2

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