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Diisopropylethylamine → HCID 90220274, Verbindung

HRID 2199785
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2199785
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:14][C@@H:15]1[CH2:20][CH2:19][CH2:18][N:17]([C:21]2[S:22][C:23]([NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)=[C:24]([C:26]([NH2:28])=[O:27])[N:25]=2)[CH2:16]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:14][C@@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]3[S:22][C:23]([NH:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)=[C:24]([C:26]([NH2:28])=[O:27])[N:25]=3)[CH2:16]2)=[O:11])=[CH:7][N:6]=1)([CH3:2])([CH3:3])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218978046-(tert-Butyl)nicotinic acidHCID 90220400HCID 90220400, Verbindung

Produkt 1

HCID 90220274HCID 90220274, VerbindungAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-tert-butylnicotinic acid (23.5 mg, 131 μmol) and 2-((R)-3-amino-piperidin-1-yl)-5-(pyridin-2-ylamino)-thiazole-4-carboxylic acid amide (38 mg, 119 μmol) in N,N-dimethylformamide (1 mL) was added diisopropylethylamine (35 μL, 200 μmol) followed by 0-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (61 mg, 161 μmol). After stirring at ambient temperature overnight under an atmosphere of argon the reaction was quenched by the addition of saturated aqueous ammonium chloride (2 mL), the mixture poured into water (5 mL) and extracted with ethyl acetate (3×3 mL). The combined organic extracts were washed with brine (2×2 mL), dried over sodium sulfate, filtered and concentrated in vacuo to a yellow solid. The crude product was purified by chromatography using a 13 g C-18 column gradient eluted from 10% acetonitrile in water up to 100% acetonitrile. The product containing fractions were combined and concentrated in vacuo and the residue lyophilized from acetonitrile/water to give (R)-2-(3-(6-tert-butylnicotinamido)piperidin-1-yl)-5-(pyridin-2-ylamino)thiazole-4-carboxamide as a pale yellow solid (37.8 mg, 66%).

Aufarbeitung

  1. customwas quenched by the addition of saturated aqueous ammonium chloride (2 mL)
  2. additionthe mixture poured into water (5 mL)
  3. extractionextracted with ethyl acetate (3×3 mL)
  4. washThe combined organic extracts were washed with brine (2×2 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to a yellow solid
  8. customThe crude product was purified by chromatography
  9. washeluted from 10% acetonitrile in water up to 100% acetonitrile
  10. additionThe product containing fractions
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ebc8dece443b46c687e40dc486ea4348
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09359345B2

Notizen zur Reaktion

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