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Diisopropylethylamine → tert-butyl 3-({3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

HRID 20502
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 20502
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][O:26][CH2:27][C@@H:28]([O:30][C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([O:40][C:41]2[CH:46]=[CH:45][C:44]([S:47]([CH3:50])(=[O:49])=[O:48])=[CH:43][CH:42]=2)[CH:39]=1)[C:34](O)=[O:35])[CH3:29].CCN(C(C)C)C(C)C.[NH2:60][C:61]1[CH:65]=[CH:64][N:63]([C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])[N:62]=1>CN(C=O)C>[CH3:25][O:26][CH2:27][C@H:28]([CH3:29])[O:30][C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([O:40][C:41]2[CH:46]=[CH:45][C:44]([S:47]([CH3:50])(=[O:49])=[O:48])=[CH:43][CH:42]=2)[CH:39]=1)[C:34]([NH:60][C:61]1[CH:65]=[CH:64][N:63]([C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])[N:62]=1)=[O:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 51358380tert-Butyl 3-amino-1H-pyrazole-1-carboxylateHCID 59263311(S)-3-(1-methoxypropan-2-yloxy)-5-(4-(methylsulfonyl)phenoxy)benzoic acid

Produkt 1

HCID 59346881
tert-butyl 3-({3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate
Ausbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HATU (375 mg, 1.17 mmol) was added to 3-{(1S)-2-methoxy-(1-methylethyl)oxy}-5-{[4-(methylsulfonyl)phenyl]oxy}benzoic acid (300 mg, 0.79 mmol) followed by addition of DMF (5 mL), DIPEA (0.35 mL) and tert-butyl 3-amino-1H-pyrazole-1-carboxylate (155 mg, 0.85 mmol) and the reaction was stirred under argon for 4 h. The solvent was evaporated and the residue was dissolved in saturated aqueous sodium hydrogencarbonate (30 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with saturated aqueous ammonium chloride (30 mL) then dried (MgSO4), filtered and evaporated. Purification by column chromatography, eluting with 50% ethyl acetate in hexanes, afforded the title compound as a colourless oil (185 mg, 43%).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in saturated aqueous sodium hydrogencarbonate (30 mL)
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous ammonium chloride (30 mL)
  5. dry with materialthen dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by column chromatography
  9. washeluting with 50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9d95d28151b146eb89a4ef05e0f4d10b
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07745475B2

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