Trifluoroacetic acid → HCID 86694444, compound

HRID 1519510Notes

Reaction equation

HRID 1519510 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH:18]([N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[CH2:19]2)=[CH:14][CH:13]=1.[C:35](O)([C:37]([F:40])([F:39])[F:38])=[O:36].FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[F:38][C:37]([F:40])([F:39])[C:35]([N:25]1[CH2:26][CH2:27][N:22]([CH:18]2[CH2:19][C:20]3[CH:21]=[C:12]([N:3]4[C:4](=[O:11])[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[C:2]4=[O:1])[CH:13]=[CH:14][C:15]=3[CH2:16][CH2:17]2)[CH2:23][CH2:24]1)=[O:36]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 86694443HCID 86694443, compound

Product 1

HCID 86694444HCID 86694444, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a flask charged with tert-butyl 4-[7-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]piperazine-1-carboxylate (300 mg, 0.65 mmol) and a stir bar was added TFA (2 mL). The mixture was allowed to stir at RT for 1 hour. LC showed complete removal of the Boc group. TFA was removed under reduced pressure, and the residue was dissolved in DCM (5 mL). To the solution was added pyridine and trifluoroacetic anhydride (0.27 mL, 2.0 mmol). LC showed formation of the desired product within 30 minutes. The product was purified by MPLC.

Workup

  1. customremoval of the Boc group
  2. customTFA was removed under reduced pressure
  3. dissolutionthe residue was dissolved in DCM (5 mL)

Sources & evidence

ORD record
ord-e55bc234e7fa40a4a70f21cc20181d87
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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