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Diethyl Ether → 2-(4-(6-((9-Cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-pyridinyl)-1-piperazinyl)ethanol

HRID 876008
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HRID 876008 반응식
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24]3[N:25]=[CH:26][C:27]4[C:32]5[CH:33]=[CH:34][N:35]=[CH:36][C:31]=5[N:30]([CH:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)[C:28]=4[N:29]=3)=[N:21][CH:22]=2)[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>C1COCC1.CO.Cl>[CH:37]1([N:30]2[C:28]3[N:29]=[C:24]([NH:23][C:20]4[N:21]=[CH:22][C:17]([N:14]5[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][OH:8])[CH2:12][CH2:13]5)=[CH:18][CH:19]=4)[N:25]=[CH:26][C:27]=3[C:32]3[CH:33]=[CH:34][N:35]=[CH:36][C:31]2=3)[CH2:38][CH2:39][CH2:40][CH2:41]1
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참가 물질

7

반응물 3

HCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 58299849N-(5-(4-(2-((tert-butyl(dimethyl)silyl)oxy)ethyl)-1-piperazinyl)-2-pyridinyl)-9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

생성물 1

HCID 582998102-(4-(6-((9-Cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl)amino)-3-pyridinyl)-1-piperazinyl)ethanol수율 79%

시약·촉매·용매 3

HCID 313
Hydrochloric Acid
용매
HCID 887Methanol용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

Compound 296 (85.0 mg, 148 mmol) was dissolved in dry THF (3 mL).). Tetrabutylammonium fluoride, 1.0M in THF (1.00 mL, 1.00 mmol) was added and the reaction stirred at room temperature for 2 hours. The solvent was removed in vacuo and silica gel chromatography (gradient elution hexanes+2.5%/0-100% ethyl acetate+2.5% TEA, then ethyl acetate+2.5% TEA/0-5% methanol) afforded a yellow solid. This residue was taken up in methanol (3 mL) and 1M ethanolic HCl (1 mL). Diethyl ether (20 mL) was added to precipitate the product, which was filtered and dried in vacuo to give compound 295 as a yellow solid (54 mg, 79%). 1H NMR (500 MHz, DMSO-d6) δ 10.75-10.97 (m, 2 H) 9.70 (s, 2 H) 9.47 (s, 1 H) 8.74 (d, J=3.67 Hz, 2 H) 8.16 (d, J=2.45 Hz, 1 H) 7.99-8.10 (m, 1 H) 7.84-7.99 (m, 1 H) 5.30-5.52 (m, 1 H) 3.81-3.96 (m, 4 H) 3.62-3.72 (m, 2 H) 3.20-3.36 (m, 6 H) 2.39-2.49 (m, 2 H) 2.02-2.20 (m, 4 H) 0.88 (d, J=6.85 Hz, 2 H) ppm.

후처리

  1. customThe solvent was removed in vacuo and silica gel chromatography (
  2. washgradient elution hexanes+2.5%/0-100% ethyl acetate+2.5% TEA
  3. customethyl acetate+2.5% TEA/0-5% methanol) afforded a yellow solid
  4. customto precipitate the product, which
  5. filtrationwas filtered
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-8f0b885be4bd40caa8512a1bfeee9375
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08980903B2

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