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

HRID 1359870노트

반응식

HRID 1359870 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][CH2:31][C:32](O)=[O:33])[C:25]=1[CH3:35])(=[O:12])=[O:11].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[N:57]1([CH2:62][C@H:63]2[CH2:67][CH2:66][CH2:65][NH:64]2)[CH2:61][CH2:60][CH2:59][CH2:58]1>CN(C=O)C.O.C([O-])(O)=O.[Na+]>[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][CH2:31][C:32](=[O:33])[N:64]2[CH2:65][CH2:66][CH2:67][C@@H:63]2[CH2:62][N:57]2[CH2:61][CH2:60][CH2:59][CH2:58]2)[C:25]=1[CH3:35])(=[O:11])=[O:12]

참가 물질

8

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 853151(R)-(-)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 590776223-{5-[5-(2,6-Dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-propionic Acid

생성물 1

HCID 590777235-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{3,5-dimethyl-4-[3-oxo-3-((r)-2-pyrrolidin-1-ylmethyl-pyrrolidin-1-yl)-propyl]-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a mixture of 3-{5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-propionic acid (178 mg, 0.33 mmol), EDAC (97 mg, 0.51 mmol) and HOBt (67 mg, 0.5 mmol) in DMF (4 mL) was added (R)-2-pyrrolidin-1-ylmethyl-pyrrolidine (106 mg, 0.68 mmol) and TEA (0.1 mL). The mixture was stirred at rt for 20 hours. The reaction was diluted with water and NaHCO3, extracted with DCM. The combined DCM was concentrated and the residue was purified on a silica gel column to give the titled compound.

후처리

  1. extractionextracted with DCM
  2. concentrationThe combined DCM was concentrated
  3. customthe residue was purified on a silica gel column

출처 및 근거

ORD 기록
ord-b819eb78c8c648e9befbd25bf24ff633
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599902B2

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