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Benzene → (S)-tert-butyl 5-((S)-(2-fluoro-4-(trifluoromethyl)phenyl)(2-(tetrahydro-2H-pyran-4-ylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)methyl)-2,2-dimethylpyrrolidine-1-carboxylate

HRID 2279551
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2279551
[C:1]([O:5][C:6]([N:8]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10][C@H:9]1[C@H:15]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[F:29])C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC=CC=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[O:53]1[CH2:58][CH2:57][CH:56]([NH:59][C:60]2[N:61]=[CH:62][C:63]3[CH2:69][CH2:68][NH:67][CH2:66][C:64]=3[N:65]=2)[CH2:55][CH2:54]1.C[N:71]([CH:73]=[O:74])C>O>[F:29][C:20]1[CH:21]=[C:22]([C:25]([F:26])([F:27])[F:28])[CH:23]=[CH:24][C:19]=1[C@H:15]([NH:71][C:73]([N:67]1[CH2:68][CH2:69][C:63]2[CH:62]=[N:61][C:60]([NH:59][CH:56]3[CH2:55][CH2:54][O:53][CH2:58][CH2:57]3)=[N:65][C:64]=2[CH2:66]1)=[O:74])[C@H:9]1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:12]([CH3:14])([CH3:13])[CH2:11][CH2:10]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 241BenzeneHCID 6228DimethylformamideHCID 199401P,P-Diphenylphosphinic azideHCID 71743546N-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amineHCID 86705537(S)-2-((S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)-2-(2-fluoro-4-(trifluoromethyl)phenyl)acetic acid

Produkt 1

HCID 86705539
(S)-tert-butyl 5-((S)-(2-fluoro-4-(trifluoromethyl)phenyl)(2-(tetrahydro-2H-pyran-4-ylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)methyl)-2,2-dimethylpyrrolidine-1-carboxylate
Ausbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 322 (0.341 g, 0.813 mmol) and benzene (8 mL) cooled 0° C. was added TEA (0.154 mL, 1.11 mmol) and diphenylphosphoryl azide (0.239 mL, 1.11 mmol) and the reaction stirred at RT for 1 h then refluxed for 3 h. The reaction was then cooled to RT and a solution of 28 (0.200 g, 0.739 mmol), TEA (0.154 mL, 1.11 mmol) and DMF (3 mL) was added, and stirred at RT for 18 h. The reaction was poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:10) to afford 0.360 g (74.9%) of (S)-tert-butyl 5-((S)-(2-fluoro-4-(trifluoromethyl)phenyl)(2-(tetrahydro-2H-pyran-4-ylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)methyl)-2,2-dimethylpyrrolidine-1-carboxylate (324).

Aufarbeitung

  1. temperaturethen refluxed for 3 h
  2. temperatureThe reaction was then cooled to RT
  3. stirringstirred at RT for 18 h
  4. extractionextracted with DCM
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by SiO2 chromatography
  9. washeluting with DCM/MeOH (500:10)

Quellen und Nachweise

ORD-Eintrag
ord-e4abadf307384326803847c0cf18abf9
Quelldatensatz
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09133187B2

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