Methanol → HCID 86655026, compound

HRID 2066900Notes

Reaction equation

HRID 2066900 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28][C:29]([OH:31])=O)=[CH:23][C:22]=3[F:32])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CO.[CH3:45][N:46]([CH3:50])[CH2:47][CH2:48][NH2:49]>ClCCCl>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([CH2:28][C:29](=[O:31])[NH:49][CH2:48][CH2:47][N:46]([CH3:50])[CH3:45])=[CH:23][C:22]=3[F:32])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 86655024HCID 86655024, compound

Product 1

HCID 86655026HCID 86655026, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

4-[1-(4-carboxymethyl-2,5-difluoro-phenyl)-piperidin-4-ylidene aminooxy]-piperidine-1-carboxylic acid isopropyl ester 75b (8 mg, 0.017 mmol) was dissolved in DCE (0.5 mL) and N,N-dimethylethylenediamine (0.01 mL). HOBt (4.5 mg, 0.034 mmol) and EDC(6.5 mg, 0.034 mmol) were added and the mixture was stirred at r.t. for 16 h. MeOH was added and the mixture purified by HPLC to give 4-(1-{4-[(2-dimethylamino-ethylcarbamoyl)-methyl]-2,5-difluoro-phenyl}-piperidin-4-ylideneaminooxy)-piperidine-1-carboxylic acid isopropyl ester 75-1. LC-MS 525.9 (MH+).

Workup

  1. customthe mixture purified by HPLC

Sources & evidence

ORD record
ord-65094a2f6ef546678e681d7d84791bab
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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