1,4-Dioxane hydrochloride → (R)-N-(2-aminoethyl)-N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamide

HRID 80994

Reaktionsgleichung

Reaktionsgleichung von HRID 80994
Cl.O1CCOCC1.[Cl:8][C:9]1[CH:44]=[CH:43][C:12]([CH2:13][N:14]([CH2:33][CH2:34][NH:35]C(=O)OC(C)(C)C)[C:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[C:24]4[C@H:31]([CH3:32])[CH2:30][CH2:29][C:25]=4[N:26]=[CH:27][N:28]=3)[CH2:19][CH2:18]2)=[O:16])=[CH:11][CH:10]=1>CO>[NH2:35][CH2:34][CH2:33][N:14]([CH2:13][C:12]1[CH:43]=[CH:44][C:9]([Cl:8])=[CH:10][CH:11]=1)[C:15]([N:17]1[CH2:18][CH2:19][N:20]([C:23]2[C:24]3[C@H:31]([CH3:32])[CH2:30][CH2:29][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:21][CH2:22]1)=[O:16]

Komponenten

4

Edukt 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67134584(R)-tert-butyl 2-(N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamido)ethylcarbamate

Produkt 1

HCID 25113724(R)-N-(2-aminoethyl)-N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamideAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of HCl/dioxane at 0° C. was added to (R)-tert-butyl 2-(N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamido)ethylcarbamate (40 mg, 0.075 mmol) in MeOH (1 mL). The reaction mixture was stirred at 25° C. for 1 hour. After removal of the solvent, the crude product was purified by preparative HPLC to afford (R)—N-(2-aminoethyl)-N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamide (32 mg, 90%). MS (ESI) m/e (M+H+) 429.2. 1H NMR: δ=8.56 (s, 1H), δ=7.23-7.56 (dd, 4H), δ=4.51 (s, 2H), δ=3.97-4.19 (m, 4H), δ=3.70 (m, 1H), δ=3.61 (m, 4H), δ=3.40-3.43 (t, 2H), 8=2.96-3.15 (m, 4H), δ=2.42 (m, 1H), δ=1.89 (m, 1H), δ=1.21-1.22 (d, 3H).

Aufarbeitung

  1. customAfter removal of the solvent
  2. customthe crude product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-05b13cc379b54b5c93b11547225a0551
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846683B2

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