Trifluoroacetic acid → 5-(3-Aminopropyl)-5-[({4-[(5-chloropyridin-2-yl)oxy]piperidin-1-yl} sulfonyl)methyl] imidazolidine-2,4-dione trifluoroacetic acid

HRID 32381Notes

Reaction equation

HRID 32381 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([S:15]([CH2:18][C:19]3([CH2:26][CH2:27][CH2:28][NH:29]C(=O)OC(C)(C)C)[C:23](=[O:24])[NH:22][C:21](=[O:25])[NH:20]3)(=[O:17])=[O:16])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>C(Cl)Cl>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[NH2:29][CH2:28][CH2:27][CH2:26][C:19]1([CH2:18][S:15]([N:12]2[CH2:13][CH2:14][CH:9]([O:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)[CH2:10][CH2:11]2)(=[O:16])=[O:17])[NH:20][C:21](=[O:25])[NH:22][C:23]1=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 231334991,1-Dimethylethyl 3-{4-[({4-[(5-chloropyridin-2-yl)oxy]piperidin-1-yl}sulfonyl)methyl]-2,5-dioxoimidazolidin-4-yl}propylcarbamate

Product 1

HCID 668512095-(3-Aminopropyl)-5-[({4-[(5-chloropyridin-2-yl)oxy]piperidin-1-yl} sulfonyl)methyl] imidazolidine-2,4-dione trifluoroacetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl 3-{4-[({4-[(5-chloropyridin-2-yl)oxy]piperidin-1-yl}sulfonyl)methyl]-2,5-dioxoimidazolidin-4-yl}propylcarbamate (426 mg, 0.78 mmol) was dissolved in 10 mL CH2Cl2 and 4 mL of TFA was added. The reaction was stirred at rt for 1 hour. The solvent was removed to give 408 mg (93%) of the title compound as a white solid.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-68446d09cacb4c1da5ffe21f08779362
Source dataset
uspto-grants-2008_09
Patent number
US07427631B2

Reaction notes

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