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

HRID 1359798노트

반응식

HRID 1359798 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].[CH:35]1([NH:38][CH2:39][C@@H:40]2[CH2:44][CH2:43][CH2:42][NH:41]2)[CH2:37][CH2:36]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH:35]1([NH:38][CH2:39][C@@H:40]2[CH2:44][CH2:43][CH2:42][N:41]2[C:31](=[O:32])[CH2:30][C:26]2[C:25]([CH3:34])=[C:24](/[CH:23]=[C:16]3\[C:17](=[O:22])[NH:18][C:19]4[C:15]\3=[CH:14][C:13]([S:10]([CH2:9][C:3]3[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])(=[O:11])=[O:12])=[CH:21][CH:20]=4)[NH:28][C:27]=2[CH3:29])[CH2:37][CH2:36]1

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59077497HCID 59077497, 화합물HCID 69869739cyclopropyl-(S)-1-pyrrolidin-2-ylmethyl-amine

생성물 1

HCID 590776623-[1-{4-[2-((s)-2-Cyclopropylaminomethyl-pyrrolidin-1-yl)-2-oxo-ethyl]-3,5-dimethyl-1h-pyrrol-2-yl}-meth-(z)-ylidene]-5-(2,6-dichloro-phenylmethanesulfonyl)-1,3-dihydro-indol-2-one수율 76.5%

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 (225 mg, 0.43 mmol), cyclopropyl-(S)-1-pyrrolidin-2-ylmethyl-amine (91 mg, 0.64 mmol), HOBt (91 mg, 0.67 mmol), EDAC (130 mg, 0.68 mmol) and TEA (0.15 mL, 1.1 mmol) in DMF was stirred at rt for 48 hours. The reaction was concentrated, diluted with sodium bicarbonate and extracted with DCM. The combined DCM was dried, concentrated and purified on a silica gel column to give 211 mg (76%) of the titled compound.

후처리

  1. concentrationThe reaction was concentrated
  2. additiondiluted with sodium bicarbonate
  3. extractionextracted with DCM
  4. dry with materialThe combined DCM was dried
  5. concentrationconcentrated
  6. custompurified on a silica gel column

출처 및 근거

ORD 기록
ord-e09c8c0e6f894fca964945505830163a
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599902B2

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