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Triethylamine → HCID 68760588, 화합물

HRID 79578
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HRID 79578 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

7

반응물 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 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 68760588
HCID 68760588, 화합물
수율 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-616206bfe79747d481f593c5d9a3e643
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841304B2

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