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Dimethylformamide → n-Methyl-10-{[2-methyl-2'-trifluoromethyl-[1,1'-biphenyl]-4-yl]carbonyl}-n-[(1-oxidopyridin-3-yl)methyl]-10,11-dihydro-5h-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 1830055
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1830055
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[C:21](C(O)=O)=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]([F:36])([F:35])[F:34].[OH:37][N:38]1[C:42]2C=[CH:44][CH:45]=[CH:46][C:41]=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C.[CH3:68][N:69]([CH3:72])[CH:70]=[O:71]>C(OCC)(=O)C>[CH3:68][N:69]([CH2:72][C:45]1[CH:44]=[N+:38]([O-:37])[CH:42]=[CH:41][CH:46]=1)[C:70]([C:21]1[N:13]2[C:12]([CH2:11][N:10]([C:8]([C:6]3[CH:5]=[CH:4][C:3]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[C:33]([F:36])([F:34])[F:35])=[C:2]([CH3:1])[CH:7]=3)=[O:9])[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14]2)=[CH:23][CH:22]=1)=[O:71]
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Komponenten

7

Edukt 5

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1027808210-(2-methyl-2'-trifluoromethyl-biphenyl-4-carbonyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid

Produkt 1

HCID 10232599
n-Methyl-10-{[2-methyl-2'-trifluoromethyl-[1,1'-biphenyl]-4-yl]carbonyl}-n-[(1-oxidopyridin-3-yl)methyl]-10,11-dihydro-5h-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of the 10-(2-methyl-2′-trifluoromethyl-biphenyl-4-carbonyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid of Example 1, Step F (0.50 g, 1.02 mmol), methyl-(1-oxy-pyridin-3-ylmethyl)-amine dihydrochloride of Step C (0.26 g, 1.23 mmol) and 1-hydroxybenzotriazole (0.16 g, 1.18 mmol) in N,N-dimethylformamide (4 mL) was added 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (0.21 g, 1.10 mmol) followed by N,N-diisopropylethyl amine (0.73 mL, 4.10 mmol). The reaction mixture was stirred overnight, diluted with ethyl acetate and washed with water and saturated aqueous sodium bicarbonate. The organic phase was then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a yellow foam. Purification by flash chromatography eluting with 2% methanol in chloroform provided 0.52 g of the title compound, which was redissolved in dichloromethane and concentrated in vacuo to give a white foam.

Aufarbeitung

  1. washwashed with water and saturated aqueous sodium bicarbonate
  2. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow foam
  6. customPurification by flash chromatography
  7. washeluting with 2% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-29f8aae8865d44509c24817b6697e3c1
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07064120B2

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