Trifluoroacetic acid → Methyl 2-amino-5-chloro-4-(piperazin-1-yl)benzoate

HRID 1808895Notes

Reaction equation

HRID 1808895 reaction equation
C(OC([NH:8][C:9]1[C:10]([C:29]([O:31][CH3:32])=[O:30])=[CH:11][C:12]([Cl:28])=[C:13]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[CH:14]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[C:12]([Cl:28])=[CH:11][C:10]=1[C:29]([O:31][CH3:32])=[O:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66692185tert-Butyl 4-(5-(tert-butoxycarbonylamino)-2-chloro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate

Product 1

HCID 66691661Methyl 2-amino-5-chloro-4-(piperazin-1-yl)benzoateYield 119.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(5-(tert-butoxycarbonylamino)-2-chloro-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate (130 mg, 0.277 mmol) and TFA (0.4 mL, 5.19 mmol) in DCM (0.4 mL) was stirred at RT for one hour. Solvent was evaporated in vacuo to give 89 mg of methyl 2-amino-5-chloro-4-(piperazin-1-yl)benzoate. HPLC/MS showed MS (ESI+) (m/z) 270 ([M+H]+).

Workup

  1. customSolvent was evaporated in vacuo

Sources & evidence

ORD record
ord-36b6d00bb3c0451fb231eb6d76c50ce0
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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