Trifluoroacetic acid → 5-(N-(2-morpholinoethyl)methylsulfonamido)thiophene-2-carboxylic acid 2,2,2-trifluoroacetic acid salt

HRID 59750Notes

Reaction equation

HRID 59750 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]([C:14]2[S:18][C:17]([C:19]([O:21]C(C)(C)C)=[O:20])=[CH:16][CH:15]=2)[S:10]([CH3:13])(=[O:12])=[O:11])[CH2:3][CH2:2]1.[C:26]([OH:32])([C:28]([F:31])([F:30])[F:29])=[O:27]>C(Cl)Cl>[F:29][C:28]([F:31])([F:30])[C:26]([OH:32])=[O:27].[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]([C:14]2[S:18][C:17]([C:19]([OH:21])=[O:20])=[CH:16][CH:15]=2)[S:10]([CH3:13])(=[O:11])=[O:12])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86703853tert-butyl 5-(N-(2-morpholinoethyl)methylsulfonamido)-thiophene-2-carboxylate

Product 1

HCID 867038565-(N-(2-morpholinoethyl)methylsulfonamido)thiophene-2-carboxylic acid 2,2,2-trifluoroacetic acid saltYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 5-(N-(2-morpholinoethyl)-methylsulfonamido)-thiophene-2-carboxylate (Int. 58) (1.3 g, 3.33 mmol) in DCM (50 ml), TFA (2.56 ml, 33.3 mmol) was added drop-wise at 0° C. and then the brown solution was stirred at RT overnight. Additional TFA (7.69 ml, 99.9 mmol) was added in two portions over 4 hours, cooling to 0° C. and stirring at RT. The volatiles were removed under vacuum to afford 5-(N-(2-morpholinoethyl)methylsulfonamido)thiophene-2-carboxylic acid 2,2,2-trifluoroacetic acid salt (Int. 59) (1.436 g, 3.21 mmol, MS/ESI+335.0 [MH]+).

Workup

  1. temperaturecooling to 0° C.
  2. stirringstirring at RT
  3. customThe volatiles were removed under vacuum

Sources & evidence

ORD record
ord-5ab995f75b0c49bcb21e2af8f1864dd5
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

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