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Water → HCID 68760588, 화합물

HRID 79562
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HRID 79562 반응식
[C:1]([O:5][C:6]([N:8]([CH:21]([CH3:23])[CH3:22])[CH2:9][C@H:10]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.C1C=CC2N(O)N=NC=2C=1.O.C(N(CC)CC)C.[CH3:54][C:55]1[O:56][C:57]([C:60]2[C:61]([N:69]3[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]3)=[C:62]3[CH:68]=[CH:67][NH:66][C:63]3=[N:64][CH:65]=2)=[N:58][N:59]=1>C(Cl)Cl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C@H:10]([C:11]([N:72]2[CH2:71][CH2:70][N:69]([C:61]3[C:60]([C:57]4[O:56][C:55]([CH3:54])=[N:59][N:58]=4)=[CH:65][N:64]=[C:63]4[NH:66][CH:67]=[CH:68][C:62]=34)[CH2:74][CH2:73]2)=[O:12])[CH2:9][N:8]([CH:21]([CH3:22])[CH3:23])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:15][CH:16]=1
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참가 물질

8

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HCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59564929(2S)-3-[tert-butoxycarbonyl(isopropyl)amino]-2-(4-chlorophenyl)propanoic acidHCID 687611122-methyl-5-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3,4-oxadiazole

생성물 1

HCID 68760588HCID 68760588, 화합물수율 27.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(S)-3-(tert-Butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoic acid (180 mg, 0.52 mmol, see Example H), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (134 mg, 0.70 mmol), HOBt.H2O (108 mg, 0.70 mmol) and triethylamine (106 mg, 1 mmol) were added to 2-methyl-5-(4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3,4-oxadiazole (100 mg, 0.36 mmol) in DCM (10 mL). The reaction was stirred at room temperature for 18 hours. After dilution with DCM, the mixture was washed with 1N HCl, 10% K2CO3 and brine. The organic phase was dried over MgSO4 and purified by chromatography (SP4, 12+M, water/ACN 90/10→10/90, 20CV) to yield (S)-tert-butyl 2-(4-chlorophenyl)-3-(4-(5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (60 mg) as a solid.

후처리

  1. washAfter dilution with DCM, the mixture was washed with 1N HCl, 10% K2CO3 and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. custompurified by chromatography (SP4, 12+M, water/ACN 90/10→10/90, 20CV)

출처 및 근거

ORD 기록
ord-ef24ca14b95b4f92926e51a5be994355
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841304B2

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