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Sodium Carbonate → HCID 68784056, 화합물

HRID 79622
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HRID 79622 반응식
[C:1]1([C:7]2[C:8]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[C:9]3[C:15]([NH:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=4)=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:31]([O:35][C:36]([NH:38][CH2:39][CH2:40][C:41](O)=[O:42])=[O:37])([CH3:34])([CH3:33])[CH3:32].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:17]([NH:16][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]=2[N:25]2[CH2:26][CH2:27][N:28]([C:41](=[O:42])[CH2:40][CH2:39][NH:38][C:36](=[O:37])[O:35][C:31]([CH3:32])([CH3:33])[CH3:34])[CH2:29][CH2:30]2)[NH:13][CH:14]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 6

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 68760217N-(5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

생성물 1

HCID 68784056HCID 68784056, 화합물수율 91.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-(5-Phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.050 g, 0.125 mmol, see Example 64), 3-(tert-butoxycarbonylamino)propanoic acid (0.0475 g, 0.251 mmol), HOBT-H2O (0.0269 g, 0.176 mmol), and EDCI (0.0313 g, 0.163 mmol) were placed in DCM (5 mL) at room temperature. DIEA (d 0.742; 0.109 mL, 0.627 mmol) was then added, and the reaction was stirred for 5 hours. The reaction was then poured into Na2CO3 and extracted into DCM. The organic fractions were dried, filtered, and concentrated to give the crude product that was purified by column chromatography (500:20 DCM:MeOH) to give tert-butyl 3-(4-(3-(nicotinamido)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate (0.065 g, 90.9% yield).

후처리

  1. extractionextracted into DCM
  2. customThe organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give the crude product that
  6. customwas purified by column chromatography (500:20 DCM:MeOH)

출처 및 근거

ORD 기록
ord-3db005b317f34e2194cfbe4bf21cbc5d
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841304B2

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