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

반응식

HRID 1695933 반응식
[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

참가 물질

9

반응물 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

생성물 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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-b410d99a72d64f888cec84ef9b3c069b
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163737B2

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