Trifluoroacetic acid → HCID 60204662, compound

HRID 2267465Notes

Reaction equation

HRID 2267465 reaction equation
[Br:1][C:2]1[C:3]([C:20]2[S:24][C:23]3[CH:25]=[CH:26][C:27]([O:29][CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]4)=[CH:28][C:22]=3[CH:21]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]2=[O:19])=[N:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[C:3]([C:20]2[S:24][C:23]3[CH:25]=[CH:26][C:27]([O:29][CH2:30][CH2:31][N:32]4[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]4)=[CH:28][C:22]=3[CH:21]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[C:15]([CH3:17])([CH3:16])[C:14](=[O:18])[NH:13][C:12]2=[O:19])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 60204661HCID 60204661, compound

Product 1

HCID 60204662HCID 60204662, compoundYield 7.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl 4-(2-(2-(5-bromo-2-(2-(5,5-dimethyl-2,4-dioxoimidazolidin-1-yl)ethylamino)-pyrimidin-4-yl)benzo[b]thiophen-5-yloxy)ethyl)piperazine-1-carboxylate (0.23 g, 3.3 mmol) dissolved in dichloromethane (3 mL) was treated with trifluoroacetic acid (3 mL) and the mixture stirred at room temperature overnight. The volatiles were removed in vacuo and the residue dissolved in dichloromethane. The organic solution was washed with water, saturated sodium bicarbonate and brine. The solution was dried with sodium sulfate and purified by column chromatography using a gradient of 8% to 20% methanol in dichloromethane to give an off-white solid (0.143 g). MS (M+H)+ 588/590.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. washThe organic solution was washed with water, saturated sodium bicarbonate and brine
  4. dry with materialThe solution was dried with sodium sulfate
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-c83ec8aa4a1044f09064137def984320
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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