Trifluoroacetic acid → 5-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide

HRID 77377Notes

Reaction equation

HRID 77377 reaction equation
FC(F)(F)C(O)=O.[CH:8]([NH:11][C:12](=[O:40])[CH2:13][NH:14][C:15]([C:17]1[CH:18]=[C:19]([N:26]2[CH2:31][C@@H:30]3[CH2:32][C@H:27]2[CH2:28][N:29]3C(OC(C)(C)C)=O)[CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])=[O:16])([CH3:10])[CH3:9]>ClCCl>[C@H:27]12[CH2:32][C@H:30]([NH:29][CH2:28]1)[CH2:31][N:26]2[C:19]1[CH:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:17]([CH:18]=1)[C:15]([NH:14][CH2:13][C:12]([NH:11][CH:8]([CH3:10])[CH3:9])=[O:40])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68160578(1S,4S)-tert-butyl 5-(3-(2-(isopropylamino)-2-oxoethylcarbamoyl)-4-nitrophenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate2×

Product 1

HCID 671150475-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamideYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroacetic acid (4.6 g, 39.5 mmol) was added to a solution of (1S,4S)-tert-butyl 5-(3-(2-(isopropylamino)-2-oxoethylcarbamoyl)-4-nitrophenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (Intermediate 5A) (1.5 g, 3.25 mmol) in dichloromethane (15 mL). The resulting solution was stirred overnight. The resultant crude material was purified using a 20 g SCX cartridge to afford 5-((1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide (984 mg, 2.72 mmol).

Workup

  1. customThe resultant crude material was purified

Sources & evidence

ORD record
ord-ab2ebee1e9304a429da32af9854b5830
Source dataset
uspto-grants-2014_09
Patent number
US08841289B2

Reaction notes

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