1,2-Dichloroethane → [(2R)-3-(2-{2-chloro-5-fluoro-6-[(4-methyl-1-piperazinyl)(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide

HRID 1366706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366706
[CH2:1]([CH:3]([CH2:20][CH2:21][CH3:22])[CH2:4][C@H:5]([CH2:9][N:10]([CH:18]=[O:19])[O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[C:6]([OH:8])=O)C.[Cl:23][C:24]1[N:29]=[C:28]([N:30]([N:37]2[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]2)[CH2:31][C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[C:27]([F:44])=[C:26]([NH:45][NH2:46])[N:25]=1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:23][C:24]1[N:25]=[C:26]([NH:45][NH:46][C:6](=[O:8])[C@H:5]([CH2:4][CH:3]2[CH2:1][CH2:22][CH2:21][CH2:20]2)[CH2:9][N:10]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:18]=[O:19])[C:27]([F:44])=[C:28]([N:30]([N:37]2[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]2)[CH2:31][C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[N:29]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 181649HOAtHCID 866370322-chloro-5-fluoro-6-hydrazino-N-(4-methyl-1-piperazinyl)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamineHCID 86637034(2R)-4-Ethyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}heptanoic acid

Produkt 1

HCID 86637033[(2R)-3-(2-{2-chloro-5-fluoro-6-[(4-methyl-1-piperazinyl)(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamideAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(2R)-4-Ethyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}heptanoic acid (0.3764 g, 1.257 mmol), 2-chloro-5-fluoro-6-hydrazino-N-(4-methyl-1-piperazinyl)-N-(1,3-thiazol-2-ylmethyl)-4-pyrimidinamine (0.1683 g), NMM (0.298 mL, 2.71 mmol), HOAt (0.074 g, 0.542 mmol), and EDC (0.104 g, 0.542 mmol) were dissolved in DMF (10 mL). The reaction was left to stir overnight. Purification by RP-HPLC provided [(2R)-3-(2-{2-chloro-5-fluoro-6-[(4-methyl-1-piperazinyl)(1,3-thiazol-2-ylmethyl)amino]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide as a brown oily solid (0.1688 g). LCMS: (M+H)+=655.4.

Aufarbeitung

  1. waitThe reaction was left
  2. customPurification by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-1d548743e8df445bac8807cef43788fb
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893056B2

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