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1,4-Dioxane hydrochloride → (2S)-2-aminomethyl-3-(4-chlorophenyl)-1-[4-(5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one dihydrochloride

HRID 1192362
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Reaktionsgleichung

Reaktionsgleichung von HRID 1192362
C([C@:8]([CH2:39][NH2:40])([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[C:25]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[CH:24][NH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:13][CH2:12]1)=[O:10])(OC(C)(C)C)=O.[ClH:41].O1CCOCC1>O1CCOCC1>[ClH:38].[ClH:41].[NH2:40][CH2:39][C@H:8]([CH2:31][C:32]1[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[C:25]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[CH:24][NH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:13][CH2:12]1)=[O:10]
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Komponenten

4

Edukt 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86598733(2S)-2-Boc-aminomethyl-3-(4-chlorophenyl)-1-[4-(5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-pip-erazin-1-yl]-propan-1-one

Produkt 1

HCID 67539010(2S)-2-aminomethyl-3-(4-chlorophenyl)-1-[4-(5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one dihydrochlorideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

To a solution of (2S)-2-Boc-aminomethyl-3-(4-chlorophenyl)-1-[4-(5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-pip-erazin-1-yl]-propan-1-one in 1.5 mL dioxane was added 1.5 mL 4M HCl/dioxane. The resulting suspension was stirred at room temperature 16 hours, after which it was concentrated to dryness. The solids were dissolved in minimal MeOH, and the product was triturated by the addition of ether. The solids were isolated by filtration through a fritted funnel with nitrogen pressure, rinsed with ether, and dried in vacuo to give (2S)-2-aminomethyl-3-(4-chlorophenyl)-1-[4-(5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-propan-1-one dihydrochloride (37 mg, 67%) a pale yellow powder. 1H NMR (D2O, 400 MHz) δ 8.18 (1H, s), 7.41 (1H, d, J 5.4 Hz), 7.30 (1H, s), 7.19 (2H, d, J 8.6 Hz), 7.06 (1H, dd, J 5.0 and 3.5 Hz), 7.01 (2H, d, J 8.0 Hz), 6.88 (1H, d, J 3.5 Hz), 3.47-3.14 (5H, m), 3.08-3.00 (3H, m), 2.86-2.77 (3H, m), 2.59 (1H, t, J 12.0 Hz), 2.13-2.06 (1H, m). LCMS (APCI+) m/z 481 [M+H]+; Rt: 1.87 min.

Aufarbeitung

  1. concentrationafter which it was concentrated to dryness
  2. dissolutionThe solids were dissolved in minimal MeOH
  3. customthe product was triturated by the addition of ether
  4. customThe solids were isolated by filtration through a fritted funnel with nitrogen pressure
  5. washrinsed with ether
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-aef514065ac74f1cbf0e6696f78c7261
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680114B2

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