Dimethylformamide → 3-(4-Ethyl-piperazin-1-yl)-N-[4-methyl-3-(9-methyl-8-oxo-8,9-dihydro-3H-3,4,9-triaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-5-trifluoromethyl-benzamide

HRID 2261194Notes

Reaction equation

HRID 2261194 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([C:8]2[C:17](=[O:18])[N:16]([CH3:19])[C:15]3[C:10](=[CH:11][N:12]=[C:13]4[NH:22][CH:21]=[CH:20][C:14]4=3)[CH:9]=2)[CH:7]=1.[CH2:24]([N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:33]=[C:34]([CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=2)[C:35](O)=[O:36])[CH2:28][CH2:27]1)[CH3:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN(C=O)C>>[CH2:24]([N:26]1[CH2:27][CH2:28][N:29]([C:32]2[CH:33]=[C:34]([CH:38]=[C:39]([C:41]([F:44])([F:42])[F:43])[CH:40]=2)[C:35]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:23])=[C:6]([C:8]3[C:17](=[O:18])[N:16]([CH3:19])[C:15]4[C:10](=[CH:11][N:12]=[C:13]5[NH:22][CH:21]=[CH:20][C:14]5=4)[CH:9]=3)[CH:7]=2)=[O:36])[CH2:30][CH2:31]1)[CH3:25]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 591985257-(5-Amino-2-methyl-phenyl)-9-methyl-3,9-dihydro-3,4,9-triaza-cyclopenta[a]naphthalen-8-oneHCID 592125183-(4-Ethyl-piperazin-1-yl)-5-trifluoromethyl-benzoic acid

Product 1

HCID 177573403-(4-Ethyl-piperazin-1-yl)-N-[4-methyl-3-(9-methyl-8-oxo-8,9-dihydro-3H-3,4,9-triaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-5-trifluoromethyl-benzamide

Procedure

A mixture of 7-(5-amino-2-methyl-phenyl)-9-methyl-3,9-dihydro-3,4,9-triaza-cyclopenta[a]naphthalen-8-one (22 mg, 0.07 mmol), 3-(4-Ethyl-piperazin-1-yl)-5-trifluoromethyl-benzoic acid (24 mg, 0.08 mmol), HATU (30 mg, 0.08 mmol) and DIEA (27 mg, 0.21 mmol) in 0.5 mmol DMF is stirred at room temperature for 2 hours. The solvent is removed by rotary evaporation. The crude product is purified by reverse phase HPLC to give the title compound as white solid. 1H NMR 400 MHz (DMSO-d6) δ 12.19 (s, 1H), 10.32 (s, 1H), 9.71 (s, 1H), 8.54 (s, 1H), 8.01 (s, 1H), 7.72 (s, 1H), 7.66 (m, 2H), 7.58 (s, 1H), 7.50 (t, 1H, J=2.8 Hz), 7.45 (s, 1H), 7.23 (d, 1H, J=8.4), 7.04 (s, 1H), 4.06 (m, 2H), 3.99 (s, 3H), 3.55 (b, 2H), 3.15 (m, 2H), 3.06 (m, 4H), 2.09 (s, 3H), 1.20 (t, 3H, J=7.2). MS m/z 589.2 (M+1).

Workup

  1. customThe solvent is removed by rotary evaporation
  2. customThe crude product is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8412f2da15134ad59e0cdc9a83d6a7d7
Source dataset
uspto-grants-2010_12
Patent number
US07846923B2

Reaction notes

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