1,2-Dichloroethane → 1-(1-(2-((5S)-2-(2-(2-(piperidin-1-yl)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one

HRID 1695933

反応式

HRID 1695933 の反応式
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:17]2[N:21]([CH2:22][CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:20](=[O:28])[C@H:19]([CH2:29][C:30]([OH:32])=O)[S:18]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:33]1[CH2:38][CH2:37][CH:36]([N:39]2[C:47]3[C:42](=[N:43][CH:44]=[CH:45][CH:46]=3)[NH:41][C:40]2=[O:48])[CH2:35][CH2:34]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.O>[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH:17]2[N:21]([CH2:22][CH2:23][C:24]([CH3:26])([CH3:25])[CH3:27])[C:20](=[O:28])[C@H:19]([CH2:29][C:30]([N:33]3[CH2:34][CH2:35][CH:36]([N:39]4[C:47]5[C:42](=[N:43][CH:44]=[CH:45][CH:46]=5)[NH:41][C:40]4=[O:48])[CH2:37][CH2:38]3)=[O:32])[S:18]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

9

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22293182Bms-973013HCID 577743712-((5S)-2-(2-(2-(piperidin-1-yl)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

生成物 1

HCID 577744631-(1-(2-((5S)-2-(2-(2-(piperidin-1-yl)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

2-((5S)-2-(2-(2-(piperidin-1-yl)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (319.0 mg, 0.685 mmol), 1-(piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (398.9 mg, 1.370 mmol), EDC (262.6 mg, 1.370 mmol), HOBt (209.8 mg, 1.370 mmol) and DIEA (354.1 mg, 477.2 μL, 2.740 mmol) in DMF (4 mL) were stirred at RT overnight. The mixture was transferred to a separatory funnel with water and EtOAc. The aq. layer was extracted with EtOAc, the organics washed with sat bicarb, brine, dried over Na2SO4, concentrated and purified by reverse phase semiprep chromatography (CH3CN/water) to give 1-(1-(2-((5S)-2-(2-(2-(piperidin-1-yl)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one. LC/MS: 666.37 (M+1) Rt=2.06 min (10-90% 3/5 min (grad/run) w/formic acid).

後処理

  1. extractionThe aq. layer was extracted with EtOAc
  2. washthe organics washed
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by reverse phase semiprep chromatography (CH3CN/water)

出典と根拠

ORDレコード
ord-b410d99a72d64f888cec84ef9b3c069b
出典データセット
uspto-grants-2012_04
特許番号
US08163737B2

関連ノート

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