1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-Chloro-N-(1,3-dioxo-2-{2-oxo-2-[4-(4-pyridinyl)piperazino]ethyl}-2,3-dihydro-1H-isoindol-4-yl)-2-thiophenecarboxamide

HRID 457739노트

반응식

HRID 457739 반응식
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[C:12](=[O:24])[N:13]([CH2:20][C:21]([OH:23])=O)[C:14]3=[O:19])=[O:8])=[CH:4][CH:3]=1.O.O[N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35]C=2N=N1.CN(C)CCCN=[C:42]=[N:43][CH2:44][CH3:45].[CH:47]([N:50](C(C)C)CC)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[C:12](=[O:24])[N:13]([CH2:20][C:21](=[O:23])[N:43]2[CH2:42][CH2:47][N:50]([C:33]4[CH:32]=[CH:31][N:27]=[CH:35][CH:34]=4)[CH2:45][CH2:44]2)[C:14]3=[O:19])=[O:8])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 12074875HCID 12074875, 화합물

생성물 1

HCID 99579765-Chloro-N-(1,3-dioxo-2-{2-oxo-2-[4-(4-pyridinyl)piperazino]ethyl}-2,3-dihydro-1H-isoindol-4-yl)-2-thiophenecarboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

0.43 g (1.18 mmol) of 2-(4-{[(5-chloro-2-thienyl)carbonyl]amino}-1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid is dissolved in 15 ml DMF, 0.2 g (1.3 equivalents) 1-hydroxy-1H-benzotriazole hydrate (HOBT) and 0.238 g of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide (EDCI) (1.3 equivalents) are added and 0.305 g (0.411 ml; 2 equivalents) of diisopropylethylamine (DIEA) is added dropwise at room temperature over a period of 15 min. The mixture is stirred at room temperature overnight, the suspension turning into a clear solution. Water is then added to the reaction mixture, the aqueous phase is extracted three times with ethyl acetate, the combined organic phases are dried and concentrated under reduced pressure and the residue is coevaporated three times with toluene. The residue is suspended in toluene, filtered and washed with toluene. Drying gives 0.458 g (76.4% of theory) of the target compound of m.p. 207° C.

후처리

  1. extractionthe aqueous phase is extracted three times with ethyl acetate
  2. customthe combined organic phases are dried
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered
  5. washwashed with toluene
  6. customDrying
  7. customgives 0.458 g (76.4% of theory) of the target compound of m.p. 207° C.

출처 및 근거

ORD 기록
ord-150dead56a8a402d8c2390f155ab8f58
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189738B2

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