O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-[4-Methoxyethoxy-3-(4-bromphenyl)aminocarbonyl-phenyl]-2-chloro-5-(2,2,2-trifluoro-1-methyl-ethyl)carbonylaminomethyl-benzamide

HRID 1846122Notes

Reaction equation

HRID 1846122 reaction equation
[F:1][C:2]([F:9])([F:8])[CH:3]([CH3:7])[C:4](O)=[O:5].[CH3:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[C:27]([CH2:29][NH2:30])[CH:26]=[CH:25][C:24]=2[Cl:31])=[CH:17][C:16]=1[C:33]([NH:35][C:36]1[CH:41]=[CH:40][C:39]([Br:42])=[CH:38][CH:37]=1)=[O:34].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:10][O:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[C:27]([CH2:29][NH:30][C:4]([CH:3]([CH3:7])[C:2]([F:9])([F:8])[F:1])=[O:5])[CH:26]=[CH:25][C:24]=2[Cl:31])=[CH:17][C:16]=1[C:33]([NH:35][C:36]1[CH:41]=[CH:40][C:39]([Br:42])=[CH:38][CH:37]=1)=[O:34]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 113209873,3,3-Trifluoro-2-methylpropanoic acidHCID 67116841N-[4-methoxyethoxy-3-(4-bromphenyl)aminocarbonyl-phenyl]-2-chloro-5-aminomethyl-benzamide

Product 1

HCID 52920451N-[4-Methoxyethoxy-3-(4-bromphenyl)aminocarbonyl-phenyl]-2-chloro-5-(2,2,2-trifluoro-1-methyl-ethyl)carbonylaminomethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to example 53d with 3,3,3-trifluoro-2-methyl-propionic acid (10 mg; 0.07 mmol); N-[4-methoxyethoxy-3-(4-bromphenyl)aminocarbonyl-phenyl]-2-chloro-5-aminomethyl-benzamide (32 mg; 0.06 mmol); TBTU (21 mg; 0.07 mmol) in TEA (25 μL; 0.18 mmol) and 3 mL DMF.

Sources & evidence

ORD record
ord-eef2551bb23c450bbe5fcb053750557a
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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