Trifluoroacetic acid → Trifluoroacetic acid

HRID 522889Notes

Reaction equation

HRID 522889 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[N:17]=[CH:16][N:15]=[C:14]([N:18]3[CH2:34][CH2:33][C:21]4([CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)[CH2:20][CH2:19]3)[N:13]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[CH2:25]1[C:21]2([CH2:20][CH2:19][N:18]([C:14]3[N:15]=[CH:16][N:17]=[C:12]([NH:11][C:7]4[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=4)[C:3]([NH:2][CH3:1])=[O:4])[N:13]=3)[CH2:34][CH2:33]2)[CH2:22][CH2:23][NH:24]1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67377136HCID 67377136, compound

Product 2

HCID 6422Trifluoroacetic acidYield 318.3%HCID 67377035HCID 67377035, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask charged with tert-butyl 8-(4-(3-(methylcarbamoyl)phenylamino)-1,3,5-triazin-2-yl)-2,8-diazaspiro[4.5]decane-2-carboxylate (300 mg, 0.642 mmol) was added DCM (5 mL), and TFA (494 mL, 6.42 mmol) respectively. The resulting mixture was stirred overnight at RT. The reaction mixture was concentrated, and the resulting solid was triturated with ethyl acetate to obtain 3-(4-(2,8-diazaspiro[4.5]decan-8-yl)-1,3,5-triazin-2-ylamino)-N-methylbenzamide as a bis-TFA salt (233 mg, 99% yield) as white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting solid was triturated with ethyl acetate

Sources & evidence

ORD record
ord-ef933e85fc864fa18761d01bdbc7844d
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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