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Trifluoroacetic acid → Ethyl 2-(4-(4-aminophenylthio)-3-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzamido)-2-phenylpropanoate

HRID 605411
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 605411
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:37]=[CH:36][C:19]([C:20]([NH:22][C:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:21])=[CH:18][C:17]=2[NH:38][C:39]2[C:40]3[CH:48]=[CH:47][C:46]([CH:49]([CH3:51])[CH3:50])=[N:45][C:41]=3[N:42]=[CH:43][N:44]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([S:15][C:16]2[CH:37]=[CH:36][C:19]([C:20]([NH:22][C:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:21])=[CH:18][C:17]=2[NH:38][C:39]2[C:40]3[CH:48]=[CH:47][C:46]([CH:49]([CH3:50])[CH3:51])=[N:45][C:41]=3[N:42]=[CH:43][N:44]=2)=[CH:13][CH:14]=1
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Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67040905Ethyl 2-(4-(4-(tert-butoxycarbonylamino)phenylthio)-3-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzamido)-2-phenylpropanoate

Produkt 1

HCID 67041064Ethyl 2-(4-(4-aminophenylthio)-3-(7-isopropylpyrido[2,3-d]pyrimidin-4-ylamino)benzamido)-2-phenylpropanoateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

The product of Example 444A (93 mg.) was reacted with trifluoroacetic acid [TFA] (0.60 mL) in dichloromethane (0.60 mL) added dropwise at room temperature then stirred at room temperature for 1 hour. The reaction mixture was concentrated and partitioned between ethyl acetate and saturated aqueous NaHCO3. The organic layer was washed with brine, dried over MgSO4, and concentrated. The residue was chromatographed on a C-18 HPLC column with a gradient elution of acetonitrile in 0.1% TFA water (0-100%). The desired fractions were combined, concentrated, dissolved in ethyl acetate, washed with saturated aqueous NaHCO3 then brine, dried over MgSO4 and concentrated to give a pale yellow amorphous solid (67 mg, 84%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.07 (t, J=6.99 Hz, 3 H) 1.34 (d, J=6.62 Hz, 6 H) 1.84 (s, 3 H) 3.15-3.29 (m, 1 H) 4.03 (q, J=7.35 Hz, 2 H) 5.59 (s, 2 H) 6.62 (d, J=8.46 Hz, 2 H) 6.84 (d, J=8.46 Hz, 1 H) 7.12 (d, J=8.46 Hz, 2 H) 7.24-7.41 (m, 4 H) 7.52 (d, J=7.35 Hz, 2 H) 7.63 (d, J=8.46 Hz, 1 H) 7.73 (dd, J=8.46, 1.84 Hz, 1 H) 7.90 (d, J=1.84 Hz, 1 H) 8.57 (s, 1 H) 8.83 (s, 1 H) 8.86 (d, J=8.46 Hz, 2 H) 10.13 (s, 1 H).

Aufarbeitung

  1. additionadded dropwise at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and saturated aqueous NaHCO3
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a C-18 HPLC column with a gradient elution of acetonitrile in 0.1% TFA water (0-100%)
  8. concentrationconcentrated
  9. dissolutiondissolved in ethyl acetate
  10. washwashed with saturated aqueous NaHCO3
  11. dry with materialbrine, dried over MgSO4
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a58c380e867b4b1883180a03d51075b3
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07910595B2

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