Tert-butyl[{3-[amino(hydroxyimino)methyl]benzyl}(methyl)amino]acetate → Tert-butyl N-(3-{5-[4-(2-ethylpiperidin-1-yl)-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate

HRID 2410575Notes

Reaction equation

HRID 2410575 reaction equation
[ClH:1].[CH2:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][C:11]=1[CH2:19][O:20][CH3:21])[CH3:3].[NH2:22][C:23](=[N:41][OH:42])[C:24]1[CH:25]=[C:26]([CH:38]=[CH:39][CH:40]=1)[CH2:27][N:28]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH3:29]>>[CH2:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:10]1[CH:18]=[CH:17][C:13]([C:14]2[O:16][N:41]=[C:23]([C:24]3[CH:25]=[C:26]([CH:38]=[CH:39][CH:40]=3)[CH2:27][N:28]([CH3:29])[CH2:30][C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[N:22]=2)=[CH:12][C:11]=1[CH2:19][O:20][CH3:21])[CH3:3].[ClH:1].[CH2:2]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][N:5]1[C:10]1[CH:18]=[CH:17][C:13]([C:14]2[O:42][N:41]=[C:23]([C:24]3[CH:25]=[C:26]([CH:38]=[CH:39][CH:40]=3)[CH2:27][N:28]([CH3:29])[CH2:30][C:31]([OH:33])=[O:32])[N:22]=2)=[CH:12][C:11]=1[CH2:19][O:20][CH3:21])[CH3:3]

Participants

4

Reactant 2

HCID 72307500Tert-butyl[{3-[amino(hydroxyimino)methyl]benzyl}(methyl)amino]acetateHCID 1317314304-(2-Ethylpiperidin-1-yl)-3-(methoxymethyl)benzoic acid hydrochloride

Product 2

HCID 66678588Tert-butyl N-(3-{5-[4-(2-ethylpiperidin-1-yl)-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinateHCID 131731799N-(3-{5-[4-(2-ethylpiperidin-1-yl)-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycine, hydrochloride salt

Procedure

Tert-butyl N-(3-{5-[4-(2-ethylpiperidin-1-yl)-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}benzyl)-N-methylglycinate was prepared following the general procedure 3 starting from Intermediate 9 and Intermediate 21. It was hydrolyzed following general procedure 8 to afford the title compound as a white powder. LC/MS (Method B): 479.4 (M+H)+, 477.4 (M−H)−. HPLC (Method A) Rt 2.74 min (Purity: 98.5%).

Sources & evidence

ORD record
ord-7f43d250d0b64240895bdccec3c07e44
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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