Trifluoroacetic acid → (R)-N-(2-Amino-5-(thiophen-2-yl)phenyl)-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)benzamide

HRID 1907694Notes

Reaction equation

HRID 1907694 reaction equation
[CH3:1][N:2]([CH3:37])[C@@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:36]=[CH:35][C:12]([C:13]([NH:15][C:16]3[CH:21]=[C:20]([C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)[CH:19]=[CH:18][C:17]=3[NH:27]C(=O)OC(C)(C)C)=[O:14])=[CH:11][CH:10]=2)[CH2:4]1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:27][C:17]1[CH:18]=[CH:19][C:20]([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)=[CH:21][C:16]=1[NH:15][C:13](=[O:14])[C:12]1[CH:35]=[CH:36][C:9]([CH2:8][N:5]2[CH2:6][CH2:7][C@@H:3]([N:2]([CH3:1])[CH3:37])[CH2:4]2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59737389(R)-tert-Butyl 2-(4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)benzamido)-4-(thiophen-2-yl)phenylcarbamate

Product 1

HCID 16752709(R)-N-(2-Amino-5-(thiophen-2-yl)phenyl)-4-((3-(dimethylamino)pyrrolidin-1-yl)methyl)benzamideYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 8 (0.198 g, 0.38 mmol) in DCM (3 mL) was added neat trifluoroacetic acid (1 mL). The solution was allowed to stir at room temperature for 90 min, concentrated (without heating), taken up in AcOEt, washed with saturated aqueous NaHCO3, brine, dried over MgSO4, filtered and concentrated to give title compound 9 (0.038 g, 24% yield).

Workup

  1. concentrationconcentrated
  2. temperature(without heating)
  3. washwashed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fc36136af9544172acc5b399c2aa2c67
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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