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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(5-Fluoro-pyridin-2-ylmethyl)-4-(3-phenyl-indole-1-sulfonyl)-benzamide

HRID 737049
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HRID 737049 반응식
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][N:31]=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[F:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][NH:28][C:23](=[O:24])[C:22]2[CH:21]=[CH:20][C:19]([S:16]([N:9]3[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8]3)(=[O:18])=[O:17])=[CH:27][CH:26]=2)=[N:31][CH:32]=1
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참가 물질

6

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 45079543(5-Fluoropyridin-2-yl)methanamineHCID 589751414-(3-Phenyl-indole-1-sulfonyl)-benzoic acid

생성물 1

HCID 58975149N-(5-Fluoro-pyridin-2-ylmethyl)-4-(3-phenyl-indole-1-sulfonyl)-benzamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매

실험 절차

Add to a stirring mixture of 4-(3-phenyl-indole-1-sulfonyl)-benzoic acid (5.0 g, 13.25 mmol) and 2-aminomethyl-5-fluoropyridine (dihydrochloride) (2.9 g, 14.57 mmol) in anhydrous methylene chloride (60 mL), EDCI (3.8 g, 19.82 mmol) and 4-DMAP (6.0 g, 49.10 mmol). Stir the resulting solution overnight at room temperature, concentrate to a paste, and partition between ethyl acetate (100 mL), water (100 mL), and brine (100 mL). Dry the organic layer over sodium sulfate and concentrate to an oil. Dissolve the oil in methylene chloride and add to a biotage 65 cartridge. Elute with 1:1 ethyl acetate/hexanes to provide isolation of the pure 3 (N-(5-Fluoro-pyridin-2-ylmethyl)-4-(3-phenyl-indole-1-sulfonyl)-benzamide as a solid, 5.7 g (89%): 1H NMR (DMSO-d6) δ 9.32 (t, J=5.9 Hz, 1H), 8.46 (d, J=2.9 Hz, 1H), 8.20 (d, J=8.3 Hz, 2H), 8.12 (s, 1H), 8.03 (m, 3H), 7.82 (d, J=7.8 Hz, 1H), 7.72 (d, J=6.8 Hz, 2H), 7.62 (dt, J=2.9, 8.8 Hz, 1H), 7.50 (t, J=7.3 Hz, 2H), 7.39 (m, 4H), 4.50 (d, J=5.9 Hz, 2H); MS (ESI) m/z 486 (m+H).

후처리

  1. concentrationconcentrate to a paste
  2. custompartition between ethyl acetate (100 mL), water (100 mL), and brine (100 mL)
  3. dry with materialDry the organic layer over sodium sulfate
  4. concentrationconcentrate to an oil
  5. dissolutionDissolve the oil in methylene chloride
  6. additionadd to a biotage 65 cartridge
  7. washElute with 1:1 ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-f0b2448fa602418f8b28e7ef2b9fc7fb
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07595339B2

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