Diisopropylethylamine → 1-{5-tert-Butyl-2-[3-(tert-butyl-dimethyl-silanyloxy)-5-chloro-phenyl]-2H-pyrazol-3-yl}-3-{(1S,4R)-4-[3-((S)-1-methyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-urea

HRID 60662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 60662
ClC(Cl)(Cl)CO[C:5](=[O:31])[NH:6][C:7]1[N:8]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH:17]=2)[N:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1.[CH3:34][N:35]1[CH2:39][CH2:38][CH2:37][C@H:36]1[C:40]1[N:44]2[CH:45]=[C:46]([O:49][C@H:50]3[C:59]4[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=4)[C@@H:53]([NH2:60])[CH2:52][CH2:51]3)[CH:47]=[CH:48][C:43]2=[N:42][N:41]=1.CCN(C(C)C)C(C)C>C1COCC1.O>[C:12]([C:10]1[CH:11]=[C:7]([NH:6][C:5]([NH:60][C@@H:53]2[C:54]3[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=3)[C@H:50]([O:49][C:46]3[CH:47]=[CH:48][C:43]4[N:44]([C:40]([C@@H:36]5[CH2:37][CH2:38][CH2:39][N:35]5[CH3:34])=[N:41][N:42]=4)[CH:45]=3)[CH2:51][CH2:52]2)=[O:31])[N:8]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([O:23][Si:24]([C:27]([CH3:28])([CH3:30])[CH3:29])([CH3:25])[CH3:26])[CH:17]=2)[N:9]=1)([CH3:15])([CH3:14])[CH3:13]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 117666105(1S,4R)-4-[3-((S)-1-Methyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-ylamineHCID 123756753{5-tert-Butyl-2-[3-(tert-butyl-dimethyl-silanyloxy)-5-chloro-phenyl]-2H-pyrazol-3-yl}-carbamic acid 2,2,2-trichloro-ethyl ester

Produkt 1

HCID 1233369991-{5-tert-Butyl-2-[3-(tert-butyl-dimethyl-silanyloxy)-5-chloro-phenyl]-2H-pyrazol-3-yl}-3-{(1S,4R)-4-[3-((S)-1-methyl-pyrrolidin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yloxy]-1,2,3,4-tetrahydro-naphthalen-1-yl}-ureaAusbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of Intermediate 62d (193 mg, 0.35 mmol) and Intermediate E (115 mg, 0.32 mmol) and DIPEA (166 μL, 0.94 mmol) in THF (3.5 mL) was stirred at reflux for 24 h. The cooled reaction mixture was diluted with water and extracted with DCM. The combined organics were dried and concentrated in vacuo to give the title compound (265 mg, 99%). LCMS (Method 3): Rt 3.82 min, m/z 769 [MH+].

Aufarbeitung

  1. temperatureat reflux for 24 h
  2. customThe cooled reaction mixture
  3. extractionextracted with DCM
  4. customThe combined organics were dried
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-15be7a23b1da461797c143608cbdbcf3
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440974B2

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