Ammonia → (S)-4-Amino-N-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethyl)tetrahydro-2H-pyran-4-carboxamide

HRID 216986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 216986
[C:1]([C@@H:3]([NH:21][C:22]([C:24]1([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17](=[O:19])[NH:16][C:15]=3[CH:20]=2)=[CH:7][CH:6]=1)#[N:2].N>C(O)=O.O>[NH2:30][C:24]1([C:22]([NH:21][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:12]=[CH:13][C:14]4[O:18][C:17](=[O:19])[NH:16][C:15]=4[CH:20]=3)=[CH:9][CH:10]=2)=[O:23])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 59568584(S)-tert-Butyl 4-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Produkt 1

HCID 59568558(S)-4-Amino-N-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethyl)tetrahydro-2H-pyran-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

(S)-tert-Butyl 4-(1-cyano-2-(4-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 33, step (ii), 160 mg) was heated at 50° C. in formic acid (0.5 mL) for 10 min. The cooled solution was diluted with water (50 mL) and basified with ‘880’ ammonia and the resulting precipitate extracted into ethyl acetate (200 mL). The dried extract was concentrated to dryness and purified purified by reversed phase HPLC (using a SunFire column) eluting with methanol/0.1% aqueous trifluoroacetic acid. The pure fractions were freeze dried to afford the titled compound as a trifluoroacetatic acid salt (36 mg) TFA salt as a colourless solid.

Aufarbeitung

  1. extractionthe resulting precipitate extracted into ethyl acetate (200 mL)
  2. extractionThe dried extract
  3. concentrationwas concentrated to dryness
  4. custompurified
  5. custompurified by reversed phase HPLC (
  6. washeluting with methanol/0.1% aqueous trifluoroacetic acid
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-38eb457326b84c719fa57a4cba17d14b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

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