Ethyl chloroacetate → HCID 59198511, compound

HRID 2261198Notes

Reaction equation

[Cl:1][C:2]1[C:12]([C:13]2[C:22](=[O:23])[N:21]([CH2:24][CH3:25])[C:20]3[C:15](=[CH:16][N:17]=[C:18]4[NH:28][CH:27]=[CH:26][C:19]4=3)[CH:14]=2)=[CH:11][C:10]([O:29][CH3:30])=[CH:9][C:3]=1[C:4]([NH:6][CH2:7][CH3:8])=[O:5].[CH2:31]([O:33][C:34](=[O:37])[CH2:35]Cl)[CH3:32].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:31]([O:33][C:34](=[O:37])[CH2:35][N:28]1[C:18]2=[N:17][CH:16]=[C:15]3[C:20]([N:21]([CH2:24][CH3:25])[C:22](=[O:23])[C:13]([C:12]4[CH:11]=[C:10]([O:29][CH3:30])[CH:9]=[C:3]([C:4](=[O:5])[NH:6][CH2:7][CH3:8])[C:2]=4[Cl:1])=[CH:14]3)=[C:19]2[CH:26]=[CH:27]1)[CH3:32]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-chloro-N-ethyl-3-(9-ethyl-8-oxo-8,9-dihydro-3H-3,4,9-triaza-cyclopenta[a]naphthalen-7-yl)-5-methoxy-benzamide (7.6 mg, 0.018 mmol), chloro-acetic acid ethyl ester (2.2 mg, 0.018 mmol), potassium carbonate (0.89 mg, 0.0064 mmol) and acetone (0.5 mL) is heated up to 60° C. for 2 h. Solvent is removed and water is added. The mixture is extracted with chloroform and methanol (20:1) and the extracts is combined and dried with MgSO4. After removal of the solvent, the residue is purified on silica gel column (ethyl acetate:hexane=4:1) to give desired product. MS m/z 511.1 (M+1). 2.5 mg of the product is hydrolyzed with LiOH.H2O in THF, MeOH and H2O at rt for 1 h to give the desired acid product. MS m/z 483.1 (M+1).

Workup

customSolvent is removed
additionwater is added
extractionThe mixture is extracted with chloroform and methanol (20:1)
dry with materialdried with MgSO4
customAfter removal of the solvent
customthe residue is purified on silica gel column (ethyl acetate:hexane=4:1)

Sources & evidence

ORD record: ord-53c1491a5a2a464cbd2634384142a4bd
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846923B2

Reaction notes

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