Hydrochloric Acid → HCID 66882565, compound

HRID 1784053Notes

Reaction equation

HRID 1784053 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:8]([C:9](=[O:18])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:7]1[C:19](=[O:40])[NH:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35](O)=[O:36])=[CH:29][C:28]2=[O:38])=[CH:23][C:22]=1[F:39])=[O:5])[CH3:2].Cl.[CH3:42][NH:43][CH3:44].ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.Cl>CN(C=O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH:7]([C:19](=[O:40])[NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35](=[O:36])[N:43]([CH3:44])[CH3:42])=[CH:29][C:28]3=[O:38])=[CH:23][C:22]=2[F:39])[CH:8]1[C:9](=[O:18])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66881221HCID 66881221, compound

Product 1

HCID 66882565HCID 66882565, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 23 mg (0.04 mmol) of (1SR,2RS,3SR) 2-[4-(4-carboxymethoxy-2-oxo-2H-pyridin-1-yl)-2-fluoro-phenylcarbamoyl]-3-(4-chloro-phenylcarbamoyl) cyclopropanecarboxylic acid ethyl ester (example 155), 5 mg (0.06 mmol) of dimethylamine hydrochloride, 1 mg of 1-hydroxybenzotriazole, and 25 ul (0.23 mmol) of N-methylmorpholine in 2.5 ml of DMF was treated with 11 mg (0.06 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and stirred at RT during 10 hrs. The mixture was poured into a 2M aqueous solution of HCl and extracted with AcOEt. Drying of the combined organic phases over Na2SO4, filtration, evaporation of the solvent and chromatography on silica gel with AcOEt/MeOH 10:1 gave 22 mg (95%) of (1SR,2RS,3SR)-2-(4-chloro-phenylcarbamoyl)-3-[4-(4-dimethylcarbamoylmethoxy-2-oxo-2H-pyridin-1-yl)-2-fluoro-phenylcarbamoyl]-cyclopropanecarboxylic acid ethyl ester. Light brown solid. MS: 600 (M+H)+.

Workup

  1. extractionextracted with AcOEt
  2. dry with materialDrying of the combined organic phases over Na2SO4, filtration, evaporation of the solvent and chromatography on silica gel with AcOEt/MeOH 10:1

Sources & evidence

ORD record
ord-4b6f7ef19e5547d19076744adbf0728d
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

Loading…