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Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → rac-tert-Butyl 1-(3-{[cyclopent-1-en-1-yl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate

HRID 626451
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Reaktionsgleichung

Reaktionsgleichung von HRID 626451
[C:1]1([CH:6]([N:10]2[CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]2)[C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH:2]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:42][C:43]1[CH:44]=[C:45]([CH:57]=[CH:58][C:59]=1[F:60])[CH2:46][C:47]1([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:49][CH2:48]1>CN(C=O)C.N1C=CC=CC=1.C(OCC)(=O)C>[C:1]1([CH:6]([N:10]2[CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]2)[C:7]([NH:42][C:43]2[CH:44]=[C:45]([CH:57]=[CH:58][C:59]=2[F:60])[CH2:46][C:47]2([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:48][CH2:49]2)=[O:9])[CH2:5][CH2:4][CH2:3][CH:2]=1
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Komponenten

6

Edukt 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58136688tert-Butyl 1-(3-amino-4-fluorobenzyl)cyclopropanecarboxylateHCID 90014907rac-Cyclopent-1-en-1-yl(4-methoxypiperidin-1-yl)acetic acid

Produkt 1

HCID 90014967rac-tert-Butyl 1-(3-{[cyclopent-1-en-1-yl(4-methoxypiperidin-1-yl)acetyl]amino}-4-fluorobenzyl)cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21954950Dimethylformamide pyridineLösungsmittel

Versuchsvorschrift

30.9 mg (0.13 mmol) of rac-cyclopent-1-en-1-yl(4-methoxypiperidin-1-yl)acetic acid were initially charged in 0.87 ml of DMF/pyridine (3:1), 63.8 mg (0.17 mmol) of HATU were added and the mixture was stirred at RT for 30 min 34.3 mg (0.13 mmol) of tert-butyl 1-(3-amino-4-fluorobenzyl)cyclopropanecarboxylate were then added, and the reaction mixture was stirred at RT overnight. The mixture was then diluted with ethyl acetate, washed repeatedly with saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by preparative HPLC (RP18 column; acetonitrile/water gradient with addition of 0.1% TFA, 10:90→95:5; run time 38 min). This gave 20.7 mg (33% of theory) of the title compound.

Aufarbeitung

  1. additionwere then added
  2. washwashed repeatedly with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC (RP18 column; acetonitrile/water gradient with addition of 0.1% TFA, 10:90→95:5; run time 38 min)

Quellen und Nachweise

ORD-Eintrag
ord-6ff21bddfdfa49129420820bf6f0ca8d
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309198B2

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