4-[2-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester → [2-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizin-1-yl]-piperazin-1-yl-methanone

HRID 1963095Notes

Reaction equation

HRID 1963095 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:17]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=3[CH3:39])=[C:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:19]3[C:24]=2[CH:23]=[CH:22][CH:21]=[CH:20]3)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:38][C:34]1[C:33]([CH3:39])=[C:32]([CH:37]=[CH:36][CH:35]=1)[CH2:31][C:17]1[C:16]([C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:15])=[C:24]2[N:19]([C:18]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH:20]=[CH:21][CH:22]=[CH:23]2

Participants

4

Reactant 1

HCID 677724864-[2-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67773669[2-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizin-1-yl]-piperazin-1-yl-methanoneYield 0.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the compound of step 5 (158 mg, 299 mmol) in DCM (8 ml) and TFA (4 ml) was stirred at room temperature for 2 h. The solvents were evaporated and the residue was purified by preparative HPLC. The fractions containing the title compound were combined and lyophilized overnight. The obtained solid was dissolved in a small quantity of MOH, mixed with 0.1 N hydrochloric acid and the mixture lyophilized overnight to give 108 mg of the title compound in the form of [2-(3-fluoro-2-methyl-benzyl)-3-phenyl-indolizin-1-yl]-piperazin-1-yl-methanone hydrochloride with the following characteristics:

Workup

  1. customThe solvents were evaporated
  2. customthe residue was purified by preparative HPLC
  3. additionThe fractions containing the title compound
  4. dissolutionThe obtained solid was dissolved in a small quantity of MOH
  5. additionmixed with 0.1 N hydrochloric acid
  6. waitthe mixture lyophilized overnight

Sources & evidence

ORD record
ord-b7c5e41288ac4d0f97701429ccba80ed
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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