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(E)-N'-(3-cyano-6-isopropylpyridin-2-yl)-N,N-dimethylformimidamide → {4-[4-(4-Bromo-phenylcarbamoyl)-2-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 605321
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 605321
[Cl:1][C:2]([Cl:33])([Cl:32])[CH2:3][O:4][C:5](=[O:31])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:29])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:16][C:15]=2[NH2:30])=[CH:9][CH:8]=1.C([C:36]1[C:37]([N:45]=[CH:46][N:47]([CH3:49])C)=[N:38][C:39]([CH:42]([CH3:44])[CH3:43])=[CH:40][CH:41]=1)#N>C(O)(=O)C>[Cl:33][C:2]([Cl:1])([Cl:32])[CH2:3][O:4][C:5](=[O:31])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:29])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:16][C:15]=2[NH:30][C:49]2[C:36]3[CH:41]=[CH:40][C:39]([CH:42]([CH3:43])[CH3:44])=[N:38][C:37]=3[N:45]=[CH:46][N:47]=2)=[CH:11][CH:12]=1
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Komponenten

4

Edukt 2

HCID 66808369(E)-N'-(3-cyano-6-isopropylpyridin-2-yl)-N,N-dimethylformimidamideHCID 67040452{4-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

Produkt 1

HCID 67040172{4-[4-(4-Bromo-phenylcarbamoyl)-2-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl esterAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176
Acetic Acid
Lösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of the products of Example 361E (2.39 g, 4.2 mmol) and Example 8E (N′-(3-cyano-6-isopropyl-pyridin-2-yl)-N,N-dimethyl-formamidine) (0.91 g, 4.2 mmol) in 10 mL of glacial acetic acid was heated in a 140° C. preheated oil bath for 45 minutes. The reaction mixture was cooled, evaporated in vacuo and the residue partitioned between ethyl acetate (250 mL) and water (100 mL). The organic phase was then washed with saturated aqueous sodium bicarbonate and then brine, dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. The resulting residue was triturated with methanol, filtered, and dried in vacuo to provide the title compound (2.0 g, 64%) as a beige solid. MS (ESI+) m/z 743/745 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.31 (d, J=6.62 Hz, 6 H), 3.10-3.27 (m, 1 H), 4.93 (s, 2 H), 6.93-7.05 (m, 3 H), 7.39-7.62 (m, 5 H), 7.77 (d, J=8.82 Hz, 2 H), 8.17 (s, 1 H), 8.60 (s, 1 H), 8.78 (d, J=8.09 Hz, 1 H), 10.08 (s, 1 H), 10.16 (s, 1 H), 10.35 (s, 2 H).

Aufarbeitung

  1. customfor 45 minutes
  2. temperatureThe reaction mixture was cooled
  3. customevaporated in vacuo
  4. customthe residue partitioned between ethyl acetate (250 mL) and water (100 mL)
  5. washThe organic phase was then washed with saturated aqueous sodium bicarbonate
  6. dry with materialbrine, dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe resulting residue was triturated with methanol
  10. filtrationfiltered
  11. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ef774315c71c40438aaf0e13163ce33e
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07910595B2

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