Sodium Bicarbonate → Tert-butyl 2-(4-((3-fluoro-5-(trifluoromethyl)benzamido)methyl)piperidin-1-yl)ethylcarbamate

HRID 1046553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1046553
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:5][CH2:4]1.[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:23](O)=[O:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O.C1COCC1.C(Cl)Cl>[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:28]=1)[C:23]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:5][CH2:4]1)=[O:24]

Komponenten

9

Edukt 4

HCID 516892Sodium BicarbonateHCID 5192223-Fluoro-5-(trifluoromethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57993236Tert-butyl 2-(4-(aminomethyl)piperidin-1-yl)ethylcarbamate

Produkt 1

HCID 57993174Tert-butyl 2-(4-((3-fluoro-5-(trifluoromethyl)benzamido)methyl)piperidin-1-yl)ethylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A solution of tert-butyl 2-(4-(aminomethyl)piperidin-1-yl)ethylcarbamate (50 mg, 0.19 mmol), TEA (135 μL, 0.972 mmol), and 3-fluoro-5-(trifluoromethyl)benzoic acid (48 mg, 0.23 mmol) in a mixture of 1:1 CH2Cl2:THF (2 mL) was treated with a solution of HATU (111 mg, 0.292 mmol) in DMF (1 mL). The resulting solution was stirred overnight, then transferred to a test tube containing saturated aqueous NaHCO3 (4 mL) and EtOAc (4 mL). The biphasic mixture was mixed vigorously and allowed to separate for 15 minutes. After separation, the mixture was cooled to −20° C. until the aqueous layer was frozen. The organic layer was then poured off and the solvent was removed under reduced pressure at 50° C. The resulting residue was purified by HiTOPs.

Aufarbeitung

  1. customtransferred to a test tube
  2. additionThe biphasic mixture was mixed vigorously
  3. customto separate for 15 minutes
  4. customAfter separation
  5. temperaturewas frozen
  6. additionThe organic layer was then poured off
  7. customthe solvent was removed under reduced pressure at 50° C
  8. customThe resulting residue was purified by HiTOPs

Quellen und Nachweise

ORD-Eintrag
ord-d7253e6292634e158350cafaead509e5
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569344B2

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