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2-(4-Chlorophenyl)ethylamine → tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-((N-methylmethylsulfonamido)methyl)phenyl)acetate

HRID 453546
Notes
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Reaction equation

HRID 453546 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][C:8]1[CH:23]=[CH:22][C:11]([O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[C:10]([CH2:24][N:25]([CH3:30])[S:26]([CH3:29])(=[O:28])=[O:27])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl:65][C:66]1[CH:71]=[CH:70][C:69]([CH2:72][CH2:73][NH2:74])=[CH:68][CH:67]=1>CN(C=O)C.O>[Cl:65][C:66]1[CH:71]=[CH:70][C:69]([CH2:72][CH2:73][NH:74][C:17]([C:16]2[CH:15]=[CH:14][C:13]([O:12][C:11]3[CH:22]=[CH:23][C:8]([CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:31])=[CH:9][C:10]=3[CH2:24][N:25]([CH3:30])[S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=2)=[O:18])=[CH:68][CH:67]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 674302-(4-Chlorophenyl)ethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 693244814-(4(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoic acid

Product 1

HCID 69321553
tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-((N-methylmethylsulfonamido)methyl)phenyl)acetate
Yield 17.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(4(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoic acid (50 mg, 0.111 mmol) and HATU (46.5 mg, 0.122 mmol) in DMF (1 ml) was added DIEA (23.2 μL, 0.133 mmol) followed by 2-(4-chlorophenyl)ethanamine (11.2 μL, 0.111 mmol). The reaction was diluted with water and extracted with ethyl acetate. The combined organics were washed with brine and dried over MgSO4. The crude product was purified by silica gel chromatography to give tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-3-((N-methylmethylsulfonamido)methyl)phenyl)acetate (0.0115 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over MgSO4
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-578a3559ce8142a7b19445c70a7139df
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492437B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes