Tert-butyl (4-(4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)butyl)carbamate → N-(4-aminobutyl)-4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamide

HRID 2093777Notes

Reaction equation

HRID 2093777 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:46]=[CH:45][C:8]([CH2:9][NH:10][C:11]2[N:16]=[C:15]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[N:14]=[C:13]([NH:23][C:24]3[CH:44]=[CH:43][C:27]([C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35]C(=O)OC(C)(C)C)=[O:29])=[CH:26][CH:25]=3)[N:12]=2)=[CH:7][CH:6]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:35][CH2:34][CH2:33][CH2:32][CH2:31][NH:30][C:28](=[O:29])[C:27]1[CH:43]=[CH:44][C:24]([NH:23][C:13]2[N:12]=[C:11]([NH:10][CH2:9][C:8]3[CH:45]=[CH:46][C:5]([O:4][CH2:3][CH2:2][Br:1])=[CH:6][CH:7]=3)[N:16]=[C:15]([O:17][CH2:18][C:19]([F:22])([F:21])[F:20])[N:14]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 68658523Tert-butyl (4-(4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)butyl)carbamate

Product 1

HCID 67284431N-(4-aminobutyl)-4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamide

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Tert-butyl (4-(4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamido)butyl)carbamate (3.0 g, 4.21 mmol) was stirred in TFA/DCM (1:1) solution (20 mL) for 1 h. The solution was concentrated under vacuum to give N-(4-aminobutyl)-4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzamide which was carried to the next step without purification.

Workup

  1. concentrationThe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-4282cc04ff284f53bd1b4e1f7dfede2a
Source dataset
uspto-grants-2013_05
Patent number
US08445490B2

Reaction notes

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