Diisopropylethylamine → Methyl 4-((4,4,4-trifluoro-1-(4-((2-hydroxy-3,3-dimethylbutyl)carbamoyl)-2-methylphenyl)butyl)amino)benzoate

HRID 1520286Notes

Reaction equation

HRID 1520286 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH:11]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:20]=1)[CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:5]([OH:7])=O.[NH2:29][CH2:30][CH:31]([OH:36])[C:32]([CH3:35])([CH3:34])[CH3:33].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C1C=CN=CC=1.O.CN(C=O)C>[F:17][C:14]([F:15])([F:16])[CH2:13][CH2:12][CH:11]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:24]=1)[C:10]1[CH:9]=[CH:8][C:4]([C:5](=[O:7])[NH:29][CH2:30][CH:31]([OH:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:3][C:2]=1[CH3:1]

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 124977321-Amino-3,3-dimethylbutan-2-olHCID 1178400353-Methyl-4-(4,4,4-trifluoro-1-((4-(methoxycarbonyl)phenyl)amino)butyl)benzoic acid

Product 1

HCID 117840033Methyl 4-((4,4,4-trifluoro-1-(4-((2-hydroxy-3,3-dimethylbutyl)carbamoyl)-2-methylphenyl)butyl)amino)benzoate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methyl-4-(4,4,4-trifluoro-1-((4-(methoxycarbonyl)phenyl)amino)butyl)benzoic acid (725.6 mg), 1-amino-3,3-dimethylbutan-2-ol (430 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (704 mg), 1-hydroxybenzotriazole monohydrate (562 mg), N,N-diisopropylethylamine (0.962 mL), 4-dimethylaminopyridine (22.42 mg) and DMF (4.5 mL) was stirred at room temperature overnight, and water was added. The mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-f5af09e5e91541398931a604e38536c9
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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