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

HRID 919583ノート

反応式

HRID 919583 の反応式
[CH2:1]([N:3]([C@H:23]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]1)[C:4]1[C:5]2[CH:12]=[CH:11][N:10]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:6]=2[N:7]=[CH:8][N:9]=1)[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:50][C:51]1[CH:52]=[C:53]([NH:58][CH2:59][C:60](O)=[O:61])[CH:54]=[C:55]([Cl:57])[CH:56]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:50][C:51]1[CH:52]=[C:53]([NH:58][CH2:59][C:60]([N:25]2[CH2:26][CH2:27][CH2:28][C@H:23]([N:3]([CH2:1][CH3:2])[C:4]3[C:5]4[CH:12]=[CH:11][N:10]([S:13]([C:16]5[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=5)(=[O:14])=[O:15])[C:6]=4[N:7]=[CH:8][N:9]=3)[CH2:24]2)=[O:61])[CH:54]=[C:55]([Cl:57])[CH:56]=1

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13138167(3,5-Dichlorophenyl)glycineHCID 118906729(S)-N-ethyl-N-(piperidin-3-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

生成物 1

HCID 86706457(S)-2-(3,5-dichlorophenylamino)-1-(3-(ethyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone収率 83.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (S)—N-ethyl-N-(piperidin-3-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (60 mg, 0.15 mmol), in DMF (5 mL), was added EDCI (34 mg, 0.18 mmol), HOBt (24 mg, 0.18 mmol), 2-(3,5-dichlorophenylamino)acetic acid (33 mg, 0.15 mmol) and DIEA (0.06 mL, 0.36 mmol) at 0° C. The reaction mixture was stirred overnight at rt. After completion of the reaction, the reaction mixture was diluted with EtOAc (25 mL) and the organic phase was washed with water (10 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give the crude compound that was purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford the titled compound (75 mg, 82%). LC-MS: m/z [M+1]=601.

後処理

  1. customAfter completion of the reaction
  2. washthe organic phase was washed with water (10 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude compound that
  6. customwas purified by column chromatography (silica gel, gradient MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-3b97322cd3ae419883c11ee7d8844959
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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