Trifluoroacetic acid → HCID 118024552, compound

HRID 58194Notes

Reaction equation

HRID 58194 reaction equation
C(O)(C(F)(F)F)=O.[CH:8]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23]C(=O)OC(C)(C)C)=[C:19]([N+:31]([O-:33])=[O:32])[CH:18]=2)[CH2:13][CH2:12]1)([CH3:10])[CH3:9]>C(Cl)Cl>[CH:8]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([N+:31]([O-:33])=[O:32])[CH:18]=2)[CH2:15][CH2:16]1)([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118034135Tert-butyl (4-(4-isopropylpiperazin-1-yl)-2-nitrophenyl)carbamate

Product 1

HCID 118024552HCID 118024552, compoundYield 115%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (3 mL) was slowly added to a stirred solution of tert-butyl (4-(4-isopropylpiperazin-1-yl)-2-nitrophenyl)carbamate (1.2 g, 3.29 mmol) in dry DCM (5 mL) under argon atmosphere at 0° C. The resulting reaction mixture was allowed to warm to room temperature and stirred for 12 hr. Reaction progress was monitored by LCMS, after completion of the reaction, excess solvents were removed under reduced pressure to afford a crude residue. The crude residue was repeatedly washed with ether to get the title compound (1 g, yield: 80.6%) as a red solid. MS (ESI): 265.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customReaction progress
  3. customafter completion of the reaction, excess solvents
  4. customwere removed under reduced pressure
  5. customto afford a crude residue
  6. washThe crude residue was repeatedly washed with ether

Sources & evidence

ORD record
ord-79f0884b750d43199b09e9cf1a9c5efc
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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