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 1359798ノート

反応式

HRID 1359798 の反応式
[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

参加物

6

反応物 4

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

生成物 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-one収率 76.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e09c8c0e6f894fca964945505830163a
出典データセット
uspto-grants-2003_07
特許番号
US06599902B2

反応ノート

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