Ethyl piperazine-1-acetate → Dasatinib Carboxylic Acid Ethyl Ester

HRID 1437116

Reaktionsgleichung

Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]2[S:11][C:12]([C:15]([NH:17][C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:25])=[O:16])=[CH:13][N:14]=2)[CH:3]=1.[CH2:26]([O:28][C:29]([CH2:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:30])[CH3:27]>CCO>[Cl:25][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([CH3:24])[C:18]=1[NH:17][C:15]([C:12]1[S:11][C:10]([NH:9][C:4]2[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([N:35]3[CH2:34][CH2:33][N:32]([CH2:31][C:29]([O:28][CH2:26][CH3:27])=[O:30])[CH2:37][CH2:36]3)[CH:3]=2)=[N:14][CH:13]=1)=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A mixture of 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide (1) (0.20 g, 0.51 mmol) and 1-(ethoxycarbonylmethyl)piperazine (3) (0.17 g, 1.01 mmol) in 4 mL of EtOH was heated with a CEM Discover® microwave at 250 W, Pmax 150° C. for 45 min. The resulting mixture was treated with EtOH (6 mL) and then stirred at rt for 1 h. The solid was collected on a filter to give 0.24 g of ethyl 2-(4-(6-(5-((2-chloro-6-methylphenyl)carbamoyl)thiazol-2-ylamino)-2-methylpyrimidin-4-yl)piperazin-1-yl)acetate (4) (89% yield). HPLC>99% pure (Rt 2.517 min); LC/MS (ES+) 530/532 (M+H, 100); 1H NMR (DMSO-d6) δ 11.48 (s, 1H), 9.86 (s, 1H), 8.22 (s, 1H), 7.40 (m, 1H), 7.28 (m, 2H), 6.06 (s, 1H), 4.10 (q, J=7.1 Hz, 2H), 3.53 (s, 4H ??), 3.29 (s, 2H), 2.59 (t, J=4.6 Hz, 4H), 2.41 (s, 3H), 2.24 (s, 3H), 1.20 (t, J=7.1 Hz, 3H); Anal. Calcd for C24H28ClN7O3S: C, 54.38; H, 5.32; Cl, 6.69; N, 18.50; S, 6.05. Found: C, 54.24; H, 5.16; Cl, 6.80; N, 18.59; S, 6.09.

Aufarbeitung

customThe solid was collected on
filtrationa filter

Quellen und Nachweise

ORD-Eintrag: ord-c22d0294d2e14533b93a34cdd27467aa
Quelldatensatz: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07622473B2

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