1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{3,5-dimethyl-4-[2-oxo-2-((s)-3-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1359813노트

반응식

HRID 1359813 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31](O)=[O:32])[C:25]=1[CH3:34])(=[O:12])=[O:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:56]1([CH2:61][C@@H:62]2[CH2:67][CH2:66][CH2:65][NH:64][CH2:63]2)[CH2:60][CH2:59][CH2:58][CH2:57]1>CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31](=[O:32])[N:64]2[CH2:65][CH2:66][CH2:67][C@@H:62]([CH2:61][N:56]3[CH2:57][CH2:58][CH2:59][CH2:60]3)[CH2:63]2)[C:25]=1[CH3:34])(=[O:12])=[O:11]

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7183063(r)-3-Pyrrolidin-1-ylmethyl-piperidineHCID 59077497HCID 59077497, 화합물

생성물 1

HCID 590775165-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{3,5-dimethyl-4-[2-oxo-2-((s)-3-pyrrolidin-1-ylmethyl-piperidin-1-yl)-ethyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one수율 85.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of {5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetic acid (156 mg, 0.3 mmol), HOBt (80 mg) and EDAC (110 mg) in DMF (4 mL) was added TEA (3 drops). After stirring at rt for 2 hours, to the mixture was added (R)-3-pyrrolidin-1-ylmethyl-piperidine (250 mg). After stirring at rt for overnight, the reaction was concentrated and dissolved in ethyl acetate. It was then washed with water and sodium bicarbonate, dried and concentrated. The residue was purified on a silica gel column to give 172 mg of the titled compound. MS m/z 667 [M−1].

후처리

  1. stirringAfter stirring at rt for overnight
  2. concentrationthe reaction was concentrated
  3. dissolutiondissolved in ethyl acetate
  4. washIt was then washed with water and sodium bicarbonate
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified on a silica gel column

출처 및 근거

ORD 기록
ord-c8e3791ac7904ebf8f75effd224959a1
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599902B2

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