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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-butyl 3-(3-((2-(4-((4-(1H-pyrazol-1-yl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoate

HRID 625418
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HRID 625418 반응식
[C:1]([O:5][C:6](=[O:41])[CH2:7][CH2:8][S:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:38]=[CH:39][CH:40]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][C:18]=1[C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][N:37]=1)[C:32](O)=[O:33])=[O:15])([CH3:4])([CH3:3])[CH3:2].[N:42]1([C:47]2[CH:52]=[CH:51][C:50]([CH2:53][NH2:54])=[CH:49][CH:48]=2)[CH:46]=[CH:45][CH:44]=[N:43]1.CCN=C=NCCCN(C)C.Cl>CN(C)C1C=CN=CC=1.ClCCl>[N:42]1([C:47]2[CH:52]=[CH:51][C:50]([CH2:53][NH:54][C:32]([C:31]3[CH:35]=[CH:36][N:37]=[C:29]([C:18]4[CH:19]=[C:20]([N:23]5[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]5)[CH:21]=[CH:22][C:17]=4[NH:16][C:14]([C:13]4[CH:12]=[C:11]([CH:40]=[CH:39][CH:38]=4)[CH2:10][S:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:41])=[O:15])[CH:30]=3)=[O:33])=[CH:49][CH:48]=2)[CH:46]=[CH:45][CH:44]=[N:43]1
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참가 물질

6

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27764834-Pyrazol-1-YL-benzylamineHCID 665867222-(2-(3-((3-Tert-butoxy-3-oxopropylthio)methyl)benzamido)-5-(piperidin-1-yl)phenyl)isonicotinic acid

생성물 1

HCID 66587472tert-butyl 3-(3-((2-(4-((4-(1H-pyrazol-1-yl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoate수율 83%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

Into a 50-mL 3-necked round-bottom flask, was placed 2-(2-(3-((3-tert-butoxy-3-oxopropylthio)methyl)benzamido)-5-(piperidin-1-yl)phenyl)isonicotinic acid (125 mg, 0.22 mmol, 1.00 equiv), (4-(1H-pyrazol-1-yl)phenyl)methanamine (41 mg, 0.24 mmol, 1.10 equiv), EDC HCl (62 mg, 0.32 mmol, 1.50 equiv), 4-dimethylaminopyridine (40 mg, 0.33 mmol, 1.51 equiv), and dichloromethane (15 mL). The resulting solution was stirred overnight at room temperature. The resulting solution was extracted with 40 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 2×15 mL of H2O. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The product was obtained as 0.132 g (83%) of a yellow crude solid.

후처리

  1. customInto a 50-mL 3-necked round-bottom flask, was placed
  2. extractionThe resulting solution was extracted with 40 mL of dichloromethane
  3. washThe resulting mixture was washed with 2×15 mL of H2O
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-51c7119c403a470ca36aef12248ee3ad
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09301951B2

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