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

HRID 1846102Notes

Reaction equation

HRID 1846102 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:24])[C:10]2[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:11]=2[N:17]2[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]2)=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:34]=[CH:33][C:32]([CH2:35][NH:36][C:37]([C:39]([CH3:42])([CH3:41])[CH3:40])=[O:38])=[CH:31][C:27]=1[C:28](O)=[O:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[CH3:23][CH:20]1[CH2:19][CH2:18][N:17]([C:11]2[CH:12]=[CH:13][C:14]([NH:16][C:28](=[O:29])[C:27]3[CH:31]=[C:32]([CH2:35][NH:36][C:37]([C:39]([CH3:40])([CH3:42])[CH3:41])=[O:38])[CH:33]=[CH:34][C:26]=3[Cl:25])=[CH:15][C:10]=2[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[O:24])[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 67116511N-(4-Bromophenyl)-2-(4-methyl-piperidin-1-yl)-5-amino-benzoic acid amide

Product 1

HCID 52919849N-[4-(4-Methyl-piperidin-1-yl)-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(tert-butylcarbonylamino)methyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 4c from N-(4-bromophenyl)-2-(4-methyl-piperidin-1-yl)-5-amino-benzoic acid amide and 2-chloro-5-(tert-butylcarbonylamino)methyl-benzoic acid with to TBTU and TEA in THF. Purification via chromatography (silica gel, eluent PE:EtOAc 6:4)

Workup

  1. customPurification via chromatography (silica gel, eluent PE:EtOAc 6:4)

Sources & evidence

ORD record
ord-c1c27695828745d2a25ac63a50270562
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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