Triethylamine → N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(2,2,2-trifluoro-1,1-dimethyl-ethyl)carbonylaminomethyl-benzamide

HRID 1846097Notes

Reaction equation

HRID 1846097 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4](O)=[O:5].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:30])[C:21]2[CH:26]=[C:25]([CH2:27][NH2:28])[CH:24]=[CH:23][C:22]=2[Cl:29])=[CH:15][C:14]=1[C:31]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([Br:40])=[CH:36][CH:35]=1)=[O:32].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:30])[C:21]2[CH:26]=[C:25]([CH2:27][NH:28][C:4]([C:3]([CH3:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[O:5])[CH:24]=[CH:23][C:22]=2[Cl:29])=[CH:15][C:14]=1[C:31]([NH:33][C:34]1[CH:35]=[CH:36][C:37]([Br:40])=[CH:38][CH:39]=1)=[O:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 198673673,3,3-Trifluoro-2,2-dimethylpropanoic acidHCID 67116388N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-aminomethyl-benzamide

Product 1

HCID 52919089N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(2,2,2-trifluoro-1,1-dimethyl-ethyl)carbonylaminomethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To 1.0 mL of a 0.13 M solution of 3,3,3-trifluoro-2,2-dimethyl-propionic acid (0.13 mmol) in DMF was added 1.0 mL of a 0.1 M solution of N-[4-methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-aminomethyl-benzamide (0.10 mmol) in DMF and triethylamine (70 μL, 0.50 mmol). Then 1.0 mL of a 0.115 M solution of TBTU (0.115 mmol) in DMF was added and the mixture was stirred overnight. The reaction mixture was directly purified via prep. HPLC to furnish the title compound.

Workup

  1. customThe reaction mixture was directly purified via prep

Sources & evidence

ORD record
ord-c8d0b647482d47a1b88604b386905b31
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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