1-Hydroxybenzotriazole → N-(6-Methyl-4'-{[2-(4-methylpiperazin-1-ylmethyl)anilino]carbonyl}-1,1'-biphenyl-3-yl)-3-furamide

HRID 970229

Reaction equation

HRID 970229 reaction equation
[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](O)=[O:22])=[CH:17][CH:16]=3)[CH:14]=2)=[O:7])=[CH:2]1.[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]2[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=2[NH2:35])[CH2:28][CH2:27]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:35][C:34]3[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=3[CH2:32][N:29]3[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]3)=[O:22])=[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

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 64845562-[(4-Methylpiperazin-1-yl)methyl]anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69152146HCID 69152146, compound

Product 1

HCID 69152273N-(6-Methyl-4'-{[2-(4-methylpiperazin-1-ylmethyl)anilino]carbonyl}-1,1'-biphenyl-3-yl)-3-furamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5′-(3-Furoylamino)-2′-methyl-1,1′-biphenyl-4-carboxylic acid (50 mg, 0.156 mmol), 2-(4-methylpiperazin-1-ylmethyl)aniline (32.0 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/methanol/triethylamine (96:2:2). Concentration of the product fractions under vacuum N-(6-methyl-4′-{[2-(4-methylpiperazin-1-ylmethyl)anilino]carbonyl}-1,1′-biphenyl-3-yl)-3-furamide (63 mg, 79%). NMR; δH [2H6]-DMSO includes 11.56,(1H, s), 9.94,(1H, s), 8.36-8.34,(2H, m), 8.02,(2H, d), 7-78,(1H, t), 7.68,(1H, dd), 7.64,(1H, d), 7.54,(2H, d), 7.35-7.25,(3H, m), 7.06,(1H, m), 6.98,(1H, m), 3.73,(2H, s), 2.22,(3H, s), 2.11, (3H, s). LCMS: retention time 2.60 min, MH+509.

Workup

  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/methanol/triethylamine (96:2:2)

Sources & evidence

ORD record
ord-bf54915c68f349b4b499051c4d031cc7
Source dataset
uspto-grants-2007_12
Patent number
US07309800B2

Linked notes

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