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Diisopropylethylamine → (s)-1-Allyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

HRID 11588
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HRID 11588 반응식
Cl.[CH2:2]([N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH2:16])[C:6]1=[O:7])[CH:3]=[CH2:4].[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22]([C:27](O)=[O:28])=[CH:21]2.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:2]([N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:16][C:27]([C:22]2[NH:23][C:24]3[C:20]([CH:21]=2)=[CH:19][C:18]([Cl:17])=[CH:26][CH:25]=3)=[O:28])[C:6]1=[O:7])[CH:3]=[CH2:4]
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참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69195858(S)-1-allyl-3-amino-3,4-dihydrocarbostyril hydrochloride

생성물 1

HCID 69195207
(s)-1-Allyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril
수율 53.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(S)-1-allyl-3-amino-3,4-dihydrocarbostyril hydrochloride (7.6 mg) was added to a mixture of tetrahydrofuran (4 mL), 5-chloroindole-2-carboxylic acid (6.9 mg), 1-hydroxy-7-azabenzotriazole (5.5 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (7.7 mg) at room temperature. Diisopropylethylamine (12 mg) was added, and the resulting yellow suspension was stirred under argon for 16 h, during which a solution formed. The solution was evaporated under vacuum and the residue was directly purified by reverse phase preparative HPLC to provide the title compound (6.5 mg). HPLC/MS [M+H]+, 380; HPLC/MS [M+Na]+, 402.

후처리

  1. customformed
  2. customThe solution was evaporated under vacuum
  3. customthe residue was directly purified by reverse phase preparative HPLC

출처 및 근거

ORD 기록
ord-516d5b56df98453cafe3dd8cb1f58999
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07098235B2

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