O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-[4-(2,2-Difluoroethyl)oxy-3-ethoxycarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide

HRID 1846086Notes

Reaction equation

HRID 1846086 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH:15]([F:17])[F:16])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:18][C:19]1[CH:27]=[CH:26][C:25]([CH2:28][NH:29][C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])=[O:31])=[CH:24][C:20]=1[C:21](O)=[O:22].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(Cl)Cl.CCO>C1COCC1>[F:17][CH:15]([F:16])[CH2:14][O:13][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:21](=[O:22])[C:20]2[CH:24]=[C:25]([CH2:28][NH:29][C:30]([C:32]([CH3:33])([CH3:35])[CH3:34])=[O:31])[CH:26]=[CH:27][C:19]=2[Cl:18])=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21584144Dichloromethane ethanolHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 58483394Ethyl 5-amino-2-(2,2-difluoroethyl)oxy-benzoate

Product 1

HCID 87275046N-[4-(2,2-Difluoroethyl)oxy-3-ethoxycarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 4c from 2 ethyl 5-amino-2-(2,2-difluoroethyl)oxy-benzoate and 2-chloro-5-(tert-butylcarbonylamino)methyl-benzoic acid with TBTU and TEA in THF. Yield: (quantitative). MS [M+H]+=497 (Cl isotope pattern); TLC: Rf=0.35 (silica gel, DCM:EtOH 19:1).

Sources & evidence

ORD record
ord-09847cd3036b437f9de5a89b3b1af009
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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