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 919583노트

반응식

HRID 919583 반응식
[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

참가 물질

8

반응물 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

생성물 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)ethanone수율 83.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3b97322cd3ae419883c11ee7d8844959
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273028B2

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