Trifluoroacetic acid → HCID 86681716, compound

HRID 571308Notes

Reaction equation

HRID 571308 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[C:20](=[O:24])[N:19]([CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])[C:18]3=[O:33])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:4][CH2:3]1.[C:34]([OH:40])([C:36]([F:39])([F:38])[F:37])=[O:35]>C(Cl)Cl>[F:37][C:36]([F:39])([F:38])[C:34]([OH:40])=[O:35].[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][N:10]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[C:20](=[O:24])[N:19]([CH2:25][C:26]([OH:28])=[O:27])[C:18]3=[O:33])[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86681715HCID 86681715, compound

Product 1

HCID 86681716HCID 86681716, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(5-(N-(2-(4-methylpiperazin-1-yl)ethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetate (140 mg, 0.291 mmol) in dry DCM (4 ml) cooled to 0° C., TFA (0.449 ml, 5.83 mmol) was added, and the mixture was stirred at room temperature for 24 hours. The volatiles were removed under vacuum and the crude residue was dried affording 2-(5-(N-(2-(4-methylpiperazin-1-yl)ethyl)methylsulfonamido)-1,3-dioxoisoindolin-2-yl)acetic acid 2,2,2-trifluoroacetic acid salt (152 mg, 0.282 mmol, 97% yield, MS/ESI+ 424.8 [MH]+).

Workup

  1. customThe volatiles were removed under vacuum
  2. dry with materialthe crude residue was dried

Sources & evidence

ORD record
ord-e3c1581ed37c4f568dc4da40ddfb43ff
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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