Diisopropylethylamine → 10-[(2'-Methoxy-2-methyl-[1,1'-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid (2,3-dihydroxy-propyl)-methyl-amide

HRID 2184447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2184447
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[C:28]([C:31](O)=[O:32])=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:11][C:10]=1[CH3:34].[CH3:35][NH:36][CH2:37][CH:38](O)[CH2:39][OH:40].[OH2:42].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[OH:42][CH:38]([CH2:39][OH:40])[CH2:37][N:36]([CH3:35])[C:31]([C:28]1[N:20]2[C:19]([CH2:18][N:17]([C:15]([C:12]3[CH:13]=[CH:14][C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[C:10]([CH3:34])[CH:11]=3)=[O:16])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21]2)=[CH:30][CH:29]=1)=[O:32]

Komponenten

8

Edukt 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27341223-(Methylamino)propane-1,2-diolHCID 27960291-Hydroxybenzotriazole hydrateHCID 1027581310-[(2'-methoxy-2-methyl-[1,1'-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid

Produkt 1

HCID 1018714110-[(2'-Methoxy-2-methyl-[1,1'-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid (2,3-dihydroxy-propyl)-methyl-amideAusbeute 18,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 10-[(2′-methoxy-2-methyl-[1,1′-biphenyl]-4-yl)carbonyl]-10,11-dihydro-5H— pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid of Step E (0.50 g, 1.10 mmol) and 3-methylamino-1,2-propanediol (0.14 mL, 1.33 mmol) in N,N-dimethylformamide (4 mL) was added 1-hydroxybenzotriazole monohydrate (0.16 g, 1.18 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.23 g, 1.20 mmol) followed by N,N-diisopropylethyl amine (0.29 mL, 1.66 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 oil. Purification by flash chromatography using a solvent system of 3% methanol in chloroform gave a white foam which was crystallized by trituration with diethyl ether-hexane to provide 0.11 g of title product as a white amorphous solid.

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 oil
  6. customPurification by flash chromatography
  7. customgave a white foam which
  8. customwas crystallized by trituration with diethyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-420fc6aa00494360b76ab850ae58a020
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900200B2

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