1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-2-(3,5-dichlorophenylamino)-1-(3-((2-hydroxyethyl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone

HRID 919574노트

반응식

HRID 919574 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([N:7]([C:11]2[C:12]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[C:13]=3[N:14]=[CH:15][N:16]=2)[CH2:8][CH2:9][OH:10])[CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:51][C:52]1[CH:53]=[C:54]([NH:59][CH2:60][C:61](O)=[O:62])[CH:55]=[C:56]([Cl:58])[CH:57]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:51][C:52]1[CH:53]=[C:54]([NH:59][CH2:60][C:61]([N:1]2[CH2:6][CH2:5][CH2:4][C@@H:3]([N:7]([CH2:8][CH2:9][OH:10])[C:11]3[C:12]4[CH:19]=[CH:18][N:17]([S:20]([C:23]5[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=5)(=[O:21])=[O:22])[C:13]=4[N:14]=[CH:15][N:16]=3)[CH2:2]2)=[O:62])[CH:55]=[C:56]([Cl:58])[CH:57]=1

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13138167(3,5-Dichlorophenyl)glycineHCID 69676526(R)-2-(piperidin-3-yl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethanol

생성물 1

HCID 69676522(R)-2-(3,5-dichlorophenylamino)-1-(3-((2-hydroxyethyl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone수율 30%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (R)-2-(piperidin-3-yl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethanol (0.9 mg, 2.2 mmol) in DMF (10 mL) was added EDCI (494 mg, 2.6 mmol), HOBt (351 mg, 2.6 mmol), 2-(3,5-dichlorophenylamino)acetic acid (475 mg, 2.16 mmol) and DIEA (0.574 ml, 3.24 mmol) at 0° C. The solution was stirred at rt over night, diluted with EtOAc (25 mL) and washed with water. The aqueous layer was extracted with EtOAc, dried (Na2SO4) and concentrated in vacuo to give a residue which was purified by column chromatography (silica gel, gradient 0-2% methanol in chloroform) to afford the titled compound (0.4 g, 30%). LCMS [M+1]: 617.

후처리

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a residue which
  6. customwas purified by column chromatography (silica gel, gradient 0-2% methanol in chloroform)

출처 및 근거

ORD 기록
ord-8599a715adf34f1d9f8b3b3870e6933a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273028B2

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