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Imidazole → 7-{4-[2-(1H-1-imidazolyl)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 51602
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HRID 51602 반응식
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CS(O[CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]([N:19]2[C:23]3[N:24]=[CH:25][N:26]=[C:27]([NH2:28])[C:22]=3[C:21]([C:29]3[CH:34]=[CH:33][C:32]([O:35][C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:31][CH:30]=3)=[CH:20]2)[CH2:15][CH2:14]1)(=O)=O.[H-].[Na+]>CN(C)C=O>[N:1]1([CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[N:24]=[CH:25][N:26]=[C:27]([NH2:28])[C:22]=4[C:21]([C:29]4[CH:30]=[CH:31][C:32]([O:35][C:36]5[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=5)=[CH:33][CH:34]=4)=[CH:20]3)[CH2:15][CH2:14]2)[CH:5]=[CH:4][N:3]=[CH:2]1
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참가 물질

5

반응물 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 227363462-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}ethyl methanesulfonate

생성물 1

HCID 227363807-{4-[2-(1H-1-imidazolyl)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine수율 63%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
40 °C

실험 절차

Imidazole (0.070 g, 1.03 mmol) was added into a solution of 2-{4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclohexyl}ethyl methanesulfonate (0.052 g, 0.10 mmol) in N,N-dimethylformamide (2 mL). The mixture was stirred at 40° C. for 5 hours. 60% Sodium hydride in mineral oil (0.021 g, 052 mmol) was added and the mixture was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was purified by preparative RP-HPLC to yield 7-{4-[2-(1H-1-imidazolyl)ethyl]cyclohexyl}-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.030 g, 0.063 mmol) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.30(s, 1H), 7.55(br, 1H), 7.44(d, 2H), 7.42(t, 2H), 7.16(t, 1H), 7.08(m, 6H), 6.95(br, 1H), 5.49(br, 2H), 4.72(m, 1H), 4.01(t, 2H), 1.99-1.71 (m, 11H); RP-HPLC (Hypersil C18, 5 μm, 100 A, 250×4.6 mm; 25%-100% over 10 min acetonitrile-0.05M ammonium acetate, 1 mL/min) Rt 9.18 min; MS: MH+ 479.

후처리

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by preparative RP-HPLC

출처 및 근거

ORD 기록
ord-3407a783e8e6424691d607de940a6385
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06713474B2

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