O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(tert-butoxycarbonylamino)methyl-benzamide

HRID 1846095Notes

Reaction equation

HRID 1846095 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[CH:4][CH:3]=1.[C:20]([O:24][C:25]([NH:27][CH2:28][C:29]1[CH:30]=[CH:31][C:32]([Cl:38])=[C:33]([CH:37]=1)[C:34](O)=[O:35])=[O:26])([CH3:23])([CH3:22])[CH3:21].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl.CCO>[CH3:18][O:17][C:11]1[CH:12]=[CH:13][C:14]([NH:16][C:34](=[O:35])[C:33]2[CH:37]=[C:29]([CH2:28][NH:27][C:25]([O:24][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:26])[CH:30]=[CH:31][C:32]=2[Cl:38])=[CH:15][C:10]=1[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)=[O:19]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584833575-(((tert-Butoxycarbonyl)amino)methyl)-2-chlorobenzoic acidHCID 61090759N-(4-Bromophenyl)-2-methoxy-5-amino-benzoic acid amide

Product 1

HCID 67116272N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(tert-butoxycarbonylamino)methyl-benzamide

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 4c from N-(4-bromophenyl)-2-methoxy-5-amino-benzoic acid amide and 5-(tert.butoxycarbonylamino)methyl-2-chloro benzoic acid with TBTU and TEA. Yield: (85%). MS [m+H]+=588 (Br/Cl-isotope pattern); TLC: Rf=0.60 (silica gel, DCM:EtOH 9:1).

Sources & evidence

ORD record
ord-18a0360058d744078e048b49ac864092
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

Loading…