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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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HRID 1192362 반응식
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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참가 물질

4

반응물 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

생성물 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 dihydrochloride수율 67%

시약·촉매·용매 1

HCID 312751,4-Dioxane
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aef514065ac74f1cbf0e6696f78c7261
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680114B2

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