1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58902261, compound

HRID 1640181Notes

Reaction equation

HRID 1640181 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH:15]([C:19]([OH:21])=O)[CH2:16]3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][CH:15]([C:19]([NH:22][C:23]4[CH:24]=[C:25]([CH:35]=[C:36]([C:38]([F:39])([F:40])[F:41])[CH:37]=4)[CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:21])[CH2:16]3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 58902359HCID 58902359, compoundHCID 59735029tert-butyl N-{[3-amino-5-(trifluoromethyl)phenyl]methyl}carbamate

Product 1

HCID 58902261HCID 58902261, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the hydrochloride salt of 7-[(2-aminopyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (1.99 g), tert-butyl [3-amino-5-(trifluoromethyl)-benzyl]carbamate (1.98 g, 6.82 mmol), and DMAP (0.834 g, 6.82 mmol) in DMF (60 mL) was added EDCI (1.31 g, 6.82 mmol). The reaction mixture was allowed to stir at rt overnight under an atmosphere of nitrogen. The reaction mixture was diluted with water and extracted with EtOAc. The organic solutions were combined, washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography to give tert-butyl [3-[({7-[(2-aminopyridin-4-yl)oxy]-1,2,3,4-tetrahydronaphthalen-2-yl}carbonyl)-amino]-5-(trifluoromethyl)benzyl]carbamate (2.45 g, 71%). LCMS: (FA) ES+ 557.9, ES+ 554.6.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c4d73594abe849f38327191af0003dea
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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