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

HRID 2264590Notes

Reaction equation

HRID 2264590 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

5

Reactant 3

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 1859152-NaphthylalanineHCID 58659388HCID 58659388, compound

Product 1

HCID 59596407HCID 59596407, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

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.

Workup

  1. concentrationThen the mixture is concentrated partially in vacuo
  2. dissolutionThe residue is dissolved in EtOAc
  3. extractionNaHCO3 and the aqueous layer extracted twice with EtOAc
  4. washThe organic layers are washed twice with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-af3506b3e54442b19c7c990ba13338e2
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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