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Triethylamine → HCID 69099565, compound

HRID 2251542
Notes
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Reaction equation

HRID 2251542 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[CH2:9][CH2:10][C:11]2[CH:25]=[CH:24][C:14]([O:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1.CCN(CC)CC.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>ClCCl>[CH3:23][C:16]([O:15][C:14]1[CH:24]=[CH:25][C:11]([CH2:10][CH2:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:45]([CH3:44])(=[O:47])=[O:46])=[CH:7][N:6]=2)[CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=2)=[CH:12][CH:13]=1)([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH3:44][S:45]([N:1]([S:45]([CH3:44])(=[O:47])=[O:46])[C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=2)[CH2:9][CH2:10][C:11]2[CH:25]=[CH:24][C:14]([O:15][C:16]([CH3:22])([CH3:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1)(=[O:47])=[O:46]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 59643282HCID 59643282, compound

Product 2

HCID 69099565HCID 69099565, compoundYield 46%HCID 69099627HCID 69099627, compoundYield 13%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-[4-(2-{(5-aminopyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (65 mg; 0.13 mmol) in 3 ml of dichloromethane was treated with Et3N (0.019 ml; 0.14 mmol) and methanesulfonyl chloride (0.011 ml; 0.14 mmol). After 30 minutes, additional amounts of Et3N (0.019 ml) and methanesulfonyl chloride (0.011 ml) were added and stirred for another 30 minutes. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and 0.5N HCl. The organic phase was washed with 0.5N HCl and brine, dried over sodium sulfate and concentrated. Purification by radial chromatography using an ethyl acetate-hexane gradient (10–70%) provided two main products: ethyl 2-methyl-2-[4-(2-{{5-[(methylsulfonyl)amino]pyridin-2-yl}[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]propanoate (10 mg; 13% yield; MS: m/z 580 (M+1)) and ethyl 2-[4-(2-{{5-[bis(methylsulfonyl)amino]pyridin-2-yl}[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (39 mg; 46% yield; MS: m/z 658 (M+1)). (Both of these products can be hydrolyzed to the title compound).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and 0.5N HCl
  3. washThe organic phase was washed with 0.5N HCl and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by radial chromatography
  7. customprovided two main products

Sources & evidence

ORD record
ord-49a2d321025c4fe2a28254510f0a4098
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07319104B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes