1,2-Dichloroethane → 1-(1-(2-((5S)-2-(2-(2-(dimethylamino)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 1695939

반응식

HRID 1695939 반응식
[CH3:1][N:2]([CH3:29])[CH2:3][CH2:4][NH:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:13]1[N:17]([CH2:18][CH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:16](=[O:24])[CH:15]([CH2:25][C:26]([OH:28])=O)[S:14]1.[NH:30]1[CH2:35][CH2:34][CH:33]([N:36]2[C:44]3[C:39](=[N:40][CH:41]=[CH:42][CH:43]=3)[NH:38][C:37]2=[O:45])[CH2:32][CH2:31]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>[CH3:29][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:13]1[N:17]([CH2:18][CH2:19][C:20]([CH3:21])([CH3:23])[CH3:22])[C:16](=[O:24])[C@H:15]([CH2:25][C:26]([N:30]2[CH2:31][CH2:32][CH:33]([N:36]3[C:44]4[C:39](=[N:40][CH:41]=[CH:42][CH:43]=4)[NH:38][C:37]3=[O:45])[CH2:34][CH2:35]2)=[O:28])[S:14]1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 22293182Bms-973013HCID 766019922-(2-(2-(2-(Dimethylamino)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

생성물 1

HCID 577743761-(1-(2-((5S)-2-(2-(2-(dimethylamino)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 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

2-(2-(2-(2-(Dimethylamino)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (125.5 mg, 0.295 mmol), 1-(piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (171.8 mg, 0.5900 mmol), EDC (113.1 mg, 0.5900 mmol), HOBt (90.35 mg, 0.5900 mmol), and DIEA (152.5 mg, 205.5 μL, 1.180 mmol) were stirred in DMF (6 mL) at RT overnight. The mixture was diluted with EtOAc and washed with water and a saturated sodium bicarbonate solution. The aqueous layer was back extracted, all organic layers were combined, washed with brine, dried over (MgSO4), concentrated to an oil. The crude oil was purified by reverse phase column chromatography with ACN/water to give desired 1-(1-(2-((5S)-2-(2-(2-(dimethylamino)ethylamino)-3-fluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetyl)piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one.

후처리

  1. washwashed with water
  2. extractionThe aqueous layer was back extracted
  3. washwashed with brine
  4. dry with materialdried over (MgSO4)
  5. concentrationconcentrated to an oil
  6. customThe crude oil was purified by reverse phase column chromatography with ACN/water

출처 및 근거

ORD 기록
ord-daa06e77ec1641ea87022aa6cf6045fb
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163737B2

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