1-Hydroxybenzotriazole → N-(6-methyl-4'-{[(3-morphlin-4-ylmethylbenzyl)amino]carbonyl}-1,1'-biphenyl-3-yl)-3-furamide

HRID 859800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 859800
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH3:24])=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([OH:23])=O)=[CH:17][CH:16]=3)[CH:14]=2)=[O:7])=[CH:2]1.[N:25]1([CH2:31][C:32]2[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=2)[CH2:35][NH2:36])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH3:24][C:12]1[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([NH:36][CH2:35][C:34]3[CH:37]=[CH:38][CH:39]=[C:32]([CH2:31][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:33]=3)=[O:23])=[CH:19][CH:20]=2)=[CH:14][C:9]([NH:8][C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[O:7])=[CH:10][CH:11]=1

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 64841823-Morpholin-4-ylmethyl-benzylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 691521465'-(3-Furoylamino)-2'-methyl-1,1'-biphenyl-4-carboxylic acid

Produkt 1

HCID 69152825N-(6-methyl-4'-{[(3-morphlin-4-ylmethylbenzyl)amino]carbonyl}-1,1'-biphenyl-3-yl)-3-furamideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

5′-(3-Furoylamino)-2′-methyl-1,1′-biphenyl-4-carboxylic acid (50 mg, 0.156 mmol), 3-(morpholin-4-ylmethyl)benzylamine (32 mg, 0.156 mmol), HATU (59.2 mg, 0.156 mmol), HOBT (21 mg, 0.156 mmol) and DIPEA (27 μl, 0.156 mmol) in DMF (2 ml) were stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate (150 ml), washed with water (2×30 ml) and dried (magnesium sulphate). The solvent was evaporated under vacuum and the residue chromatographed on a silica flash column eluting with DCM/methanoltriethylamine (96:2:2). Concentration of the product fractions under vacuum gave N-(6-methyl-4′-{[(3-morphlin-4-ylmethylbenzyl)amino]carbonyl}-1,1′-biphenyl-3-yl)-3-furamide (51 mg, 81%). NMR; δH [2H6]-DMSO 9.92,(1H, s), 9.11,(1H, t), 8.35,(1H, s), 7.97,(2H, d), 7.78,(1H, t), 7.66,(1H, dd), 7.60,(1H, d), 7.46,(2H, d), 7.28,(3H, m), 7.22,(1H, d), 7.17,(1H, d), 6.98,(1H, m), 4.50,(2H, d), 3.54,(4H, m), 3.43,(2H, s), 2.33,(4H, m), 2.19,(3H, s). LCMS: retention time 2.40 min, MH+510.

Aufarbeitung

  1. washwashed with water (2×30 ml)
  2. dry with materialdried (magnesium sulphate)
  3. customThe solvent was evaporated under vacuum
  4. customthe residue chromatographed on a silica flash column
  5. washeluting with DCM/methanoltriethylamine (96:2:2)

Quellen und Nachweise

ORD-Eintrag
ord-36b1ea8ac4a74a569d9b4eb74eb9e6f6
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07151118B2

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