Triethylamine → 3-[2-(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetylamino]-propionic acid ethyl ester

HRID 76039

Reaktionsgleichung

Reaktionsgleichung von HRID 76039
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][CH2:6][NH2:7])[CH3:2].CCN(CC)CC.[Cl:16][C:17]1[CH:18]=[C:19]([NH:23][C:24]2[O:25][C:26]([C:29]3[CH:34]=[CH:33][C:32]([CH:35]4[CH2:40][CH2:39][CH:38]([CH2:41][C:42](O)=[O:43])[CH2:37][CH2:36]4)=[CH:31][CH:30]=3)=[CH:27][N:28]=2)[CH:20]=[CH:21][CH:22]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.O>[CH2:1]([O:3][C:4](=[O:8])[CH2:5][CH2:6][NH:7][C:42](=[O:43])[CH2:41][CH:38]1[CH2:37][CH2:36][CH:35]([C:32]2[CH:31]=[CH:30][C:29]([C:26]3[O:25][C:24]([NH:23][C:19]4[CH:20]=[CH:21][CH:22]=[C:17]([Cl:16])[CH:18]=4)=[N:28][CH:27]=3)=[CH:34][CH:33]=2)[CH2:40][CH2:39]1)[CH3:2]

Komponenten

9

Edukt 5

HCID 8471TriethylamineHCID 81531DiisopropylethylamineHCID 419889Ethyl 3-aminopropanoateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57899099(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid

Produkt 1

HCID 666158633-[2-(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetylamino]-propionic acid ethyl esterAusbeute 113 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-aminopropionic acid ethyl ester (41 mg, 0.268 mmol) and Et3N (0.082 mL, 0.730 mmol) is added a solution of (4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid (100 mg, 0.243 mmol) in DMF (4 mL), HATU (102 mg, 0.268 mmol) and iPr2NEt (0.127 mL, 0.73 mmol). The reaction mixture is allowed to stir at ambient temperature for 18 h. Water is added and EtOAc is used to extract. The organic layer is washed with brine, dried with Na2SO4 and concentrated to give the title compound (140 mg) as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02-1.13 (m, 2H) 1.18 (t, J=7.07 Hz, 3H) 1.38-1.50 (m, 2H) 1.71 (dd, J=7.71, 4.17 Hz, 1H) 1.78 (t, J=12.63 Hz, 4H) 1.98 (d, J=6.57 Hz, 2H) 2.44 (t, J=6.82 Hz, 2H) 3.25-3.28 (m, 2H) 4.06 (q, J=7.07 Hz, 2H) 6.99 (ddd, J=7.89, 1.96, 1.01 Hz, 1H) 7.27-7.35 (m, 1H) 7.29 (d, J=8.59 Hz, 2H) 7.40 (s, 1H) 7.50 (d, J=8.34 Hz, 1H) 7.47-7.52 (m, 1H) 7.85 (t, J=2.02 Hz, 1H) 7.88 (t, J=5.81 Hz, 1H) 10.52 (s, 1H); (M+H)+510.2.

Aufarbeitung

  1. extractionto extract
  2. washThe organic layer is washed with brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c53c386839574ef6b0686e9f992c0bb2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835451B2

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