Trifluoroacetic acid → 2-(2-(Dibutylamino)pyrimidin-4-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoic acid

HRID 529039Notes

Reaction equation

HRID 529039 reaction equation
[CH2:1]([N:5]([CH2:41][CH2:42][CH2:43][CH3:44])[C:6]1[N:11]=[C:10]([C:12]2[CH:24]=[CH:23][C:22]([C:25](=[O:40])[NH:26][S:27]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)(=[O:29])=[O:28])=[CH:21][C:13]=2[C:14]([O:16]C(C)(C)C)=[O:15])[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:5]([CH2:41][CH2:42][CH2:43][CH3:44])[C:6]1[N:11]=[C:10]([C:12]2[CH:24]=[CH:23][C:22]([C:25](=[O:40])[NH:26][S:27]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)(=[O:28])=[O:29])=[CH:21][C:13]=2[C:14]([OH:16])=[O:15])[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060816Tert-butyl 2-(2-(dibutylamino)pyrimidin-4-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoate

Product 1

HCID 710607202-(2-(Dibutylamino)pyrimidin-4-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(2-(dibutylamino)pyrimidin-4-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoate (110 mg, 0.18 mmol) in DCM (2.0 mL) was added TFA (2.0 mL). The reaction mixture was stirred at room temperature for 3 h and concentrated in vacuo to give the title compound (95 mg, 95%), which was used in subsequent reaction without purification. MS(ESI+) m/z 561.2 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc3c205aacdf4b25a1af7ec0ff1f4d6d
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

Loading…