Trifluoroacetic acid → [6-Fluoro-3-methyl-4-(piperazine-1-carbonyl)-naphthalen-2-yl]-acetic acid methyl ester trifluoroacetate

HRID 1929579Notes

Reaction equation

HRID 1929579 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=3)[CH:19]=[C:18]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[C:17]=2[CH3:32])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36]>ClCCl>[F:33][C:34]([F:39])([F:38])[C:35]([OH:37])=[O:36].[CH3:31][O:30][C:28](=[O:29])[CH2:27][C:18]1[C:17]([CH3:32])=[C:16]([C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:15])[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([F:26])[CH:24]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593267254-(7-Fluoro-3-methoxycarbonylmethyl-2-methyl-naphthalene-1-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67367468[6-Fluoro-3-methyl-4-(piperazine-1-carbonyl)-naphthalen-2-yl]-acetic acid methyl ester trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(7-fluoro-3-methoxycarbonylmethyl-2-methyl-naphthalene-1-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester (410 mg, 0.92 mmol) in dichloromethane (10 mL) was treated with trifluoroacetic acid (2.5 mL) at room temperature, and stirred for 4 hours. The resulting mixture was concentrated in vacuo to afford [6-fluoro-3-methyl-4-(piperazine-1-carbonyl)-naphthalen-2-yl]-acetic acid methyl ester trifluoroacetate as a viscous oil which was used in the next step without further purification.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ac8813c1326c4f67aec195e744e8b413
Source dataset
uspto-grants-2012_05
Patent number
US08188090B2

Reaction notes

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