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 919574ノート

反応式

HRID 919574 の反応式
[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

参加物

8

反応物 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

生成物 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)ethanone収率 30%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8599a715adf34f1d9f8b3b3870e6933a
出典データセット
uspto-grants-2016_03
特許番号
US09273028B2

反応ノート

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