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

反応式

HRID 1695939 の反応式
[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

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-daa06e77ec1641ea87022aa6cf6045fb
出典データセット
uspto-grants-2012_04
特許番号
US08163737B2

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