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Benzylamine → N-Benzyl-3-[benzyl-(1-methyl-1H-imidazole-4-sulfonyl)-amino]-benzamide

HRID 1186258
Notes
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Reaction equation

HRID 1186258 reaction equation
[CH2:1]([N:8]([S:18]([C:21]1[N:22]=[CH:23][N:24]([CH3:26])[CH:25]=1)(=[O:20])=[O:19])[C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH2:60]([NH2:67])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>C(#N)C>[CH2:60]([NH:67][C:12](=[O:13])[C:11]1[CH:15]=[CH:16][CH:17]=[C:9]([N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[S:18]([C:21]2[N:22]=[CH:23][N:24]([CH3:26])[CH:25]=2)(=[O:20])=[O:19])[CH:10]=1)[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673189643-[Benzyl-(1-methyl-1H-imidazole-4-sulfonyl)-amino]-benzoic acid

Product 1

HCID 46182503N-Benzyl-3-[benzyl-(1-methyl-1H-imidazole-4-sulfonyl)-amino]-benzamide
Yield 4.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-[Benzyl-(1-methyl-1H-imidazole-4-sulfonyl)-amino]-benzoic acid (50 mg, 1.3 mmol), HATU (77 mg, 0.2 mmol), diisopropylethylamine (74 μL, 0.4 mmol) and benzylamine (22 μL, 0.2 mmol) were heated in dry acetonitrile under nitrogen at 60° C. for 18 hrs. After cooling, solvent was removed in vacuo and the residue purified by preparative TLC (100% ethyl acetate), to afford the title compound as a colourless oil (4.3 mg). HPLC retention time 5.46 min. Mass spectrum (ES+) m/z 462 (M+H).

Workup

  1. temperatureAfter cooling
  2. customsolvent was removed in vacuo
  3. customthe residue purified by preparative TLC (100% ethyl acetate)

Sources & evidence

ORD record
ord-58123a06ab0c42a68f130305cabd0489
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08673901B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes