Trifluoroacetic acid → 5''-(4-Piperazin-1-ylmethyl-phenyl)-[2,2';4',3'']terpyridin-6'-ylamine

HRID 1798534Notes

Reaction equation

HRID 1798534 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]([C:27]4[CH:32]=[C:31]([NH2:33])[N:30]=[C:29]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=5)[CH:28]=4)[CH:24]=[N:25][CH:26]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:11]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]([C:27]4[CH:32]=[C:31]([NH2:33])[N:30]=[C:29]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=5)[CH:28]=4)[CH:24]=[N:25][CH:26]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687592934-[4-(6'-Amino-[2,2';4',3'']terpyridin-5''-yl)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 687585475''-(4-Piperazin-1-ylmethyl-phenyl)-[2,2';4',3'']terpyridin-6'-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[4-(6′-Amino-[2,2′;4′,3″]terpyridin-5″-yl)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester (1.0 eq, 0.105 mmol, 55.1 mg) in DCM (1.0 ml) is added TFA (24.0 eq, 2.60 mmol, 0.2 ml). The reaction mixture is allowed to stir at room temperature for 30 minutes. The organic solvent is reduced in vacuo. The residue is purified by reverse phase chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA). The appropriate fractions by HPLC are combined and concentrated in vacuo. The resulting residue is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH and 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 423.

Workup

  1. customThe residue is purified by reverse phase chromatography (Isolute™ C18, 0-20% acetonitrile in water—0.1% TFA)
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting residue is dissolved in MeOH
  4. washeluting with MeOH and 2M NH3 in MeOH
  5. concentrationconcentrated in vacuo
  6. customdried under vacuum

Sources & evidence

ORD record
ord-3904a4d7db4e4e988e100a5d7bbd08ab
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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