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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 79184
ノート
印刷プレビュー

反応式

HRID 79184 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 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)ethanol収率 79.6%

試薬・触媒・溶媒 3

HCID 313
Hydrochloric Acid
溶媒
HCID 887Methanol溶媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Compound 296 (85.0 mg, 148 μmol) 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.

後処理

  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

出典と根拠

ORDレコード
ord-637768d8884d4c6e833a5298a2ec051f
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841312B2

反応ノート

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