1,4-Dioxane hydrochloride → N-(2-{[3-(fluoromethyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide HCl salt

HRID 1016080Notes

Reaction equation

HRID 1016080 reaction equation
[F:1][CH2:2][C:3]1([NH:15][C:16](=[O:31])[CH2:17][NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.O1CCOCC1.[ClH:38]>C1COCC1>[ClH:38].[F:1][CH2:2][C:3]1([NH:15][C:16](=[O:31])[CH2:17][NH:18][C:19](=[O:30])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)[CH2:7][CH2:6][NH:5][CH2:4]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59556186Tert-butyl 3-(fluoromethyl)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidine-1-carboxylate

Product 1

HCID 66792273N-(2-{[3-(fluoromethyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide HCl salt

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 578 mg (1.29 mmol) of tert-butyl 3-(fluoromethyl)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidine-1-carboxylate in 5 mL of THF was added 2 mL of 4 N HCl dioxane solution. The reaction mixture was stirred at room temperature for 1 h and evaporated to give the yellow solid, N-(2-{[3-(fluoromethyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide HCl salt: MS (m/e): 347 (M+1)+.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-d394149014e64a7fa907606ab9639455
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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