Dichloromethane → HCID 59204949, compound

HRID 2241915Notes

Reaction equation

HRID 2241915 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[C:18]([O:22][C:23](=[O:39])[NH:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][C:32]=2[F:38])[CH2:27][CH2:26]1)([CH3:21])([CH3:20])[CH3:19].Cl.C(N=C=NCCCN(C)C)C.ClCCl>CN(C)C1C=CN=CC=1.O>[C:18]([O:22][C:23](=[O:39])[NH:24][CH:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:7](=[O:9])[C:6]3[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:33][C:32]=2[F:38])[CH2:27][CH2:26]1)([CH3:21])([CH3:19])[CH3:20]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59204987HCID 59204987, compoundHCID 59205047HCID 59205047, compound

Product 1

HCID 59204949HCID 59204949, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-chloro-2-(2-methoxyethoxymethoxy)benzoic acid (compound of Reference Example 140; 0.18 g, 0.7 mmol), [1-(4-amino-2-fluorophenyl)piperidin-4-yl]carbamic acid tert-butyl ester (compound of Reference Example 90; 0.28 g, 0.9 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.17 g, 0.9 mmol), 4-dimethylaminopyridine (0.01 g) and dichloromethane (5 ml) was stirred at room temperature for 18 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give the title compound (0.27 g, 70%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-9cc340075af0494f83393765a78b3cbc
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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