1-(3-Aminopropyl)-4-methylpiperazine → HCID 59596407, compound

Reaction equation

[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[C:26](Cl)[N:25]=[CH:24][N:23]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[NH2:31][CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]1.N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>C(O)(C)C>[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[CH:27]=[C:26]([NH:31][CH2:32][CH2:33][CH2:34][N:35]5[CH2:36][CH2:37][N:38]([CH3:41])[CH2:39][CH2:40]5)[N:25]=[CH:24][N:23]=4)=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

Procedure

304 ring (0.70 mMol) of 5-(6-Chloro-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide (WO 03/099771; Stage 163), 477 μl (2.8 mMol) 1-(3-aminopropyl)-4-methyl-piperazine and a trace of Nal are heated in 10 ml isopropanol for 22 h at 50° C. Then the mixture is concentrated partially in vacuo. The residue is dissolved in EtOAc and NaHCO3 and the aqueous layer extracted twice with EtOAc. The organic layers are washed twice with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; CH2Cl2/MeOH/NH3conc. 9:1:0→90:10:1) gives the title compound: m.p.: 163° C.; MS: [M+1]+=556; TLC(CH2Cl2/MeOH/NH3conc. 90:10:2): Rf=0.29.