Trifluoroacetic acid → (R)-N-{2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-acetyl}methanesulfonamide

HRID 1351930Notes

Reaction equation

HRID 1351930 reaction equation
[CH3:1][S:2]([NH:5][C:6](=[O:29])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([NH:21]C(=O)OC(C)(C)C)[CH3:20])(=[O:4])=[O:3].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:21][C@H:19]([CH3:20])[CH2:18][C:14]1[C:13]2[C:17](=[C:9]([O:8][CH2:7][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:29])[CH:10]=[CH:11][CH:12]=2)[NH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86604018tert-butyl (R)-{2-[7-(2-methanesulfonylamino-2-oxo-ethoxy)-1H-indol-3-yl]-1-methylethyl}carbamate

Product 1

HCID 69456022(R)-N-{2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-acetyl}methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (R)-{2-[7-(2-methanesulfonylamino-2-oxoethoxy)-1H-indol-3-yl]-1-methylethyl}carbamate (0.14 g, 0.33 mmol) and trifluoroacetic acid (1 mL) in methylene chloride (4 mL) is stirred at room temperature for 8 hours. The mixture is concentrated to give the desired (R)—N-{2-[3-(2-aminopropyl)-1H-indol-7-yloxy]acetyl}methane-sulfonamide.trifluoroacetate (0.13 g, yield: 90%).

Workup

  1. concentrationThe mixture is concentrated

Sources & evidence

ORD record
ord-91750a80a6574322bb9f3af532d9ea83
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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