Formate → rac-N-(3-{4-[5-(4-dimethylaminomethyl-3-methoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 1958825Notes

Reaction equation

HRID 1958825 reaction equation
C(C1C=C(C2O[N:12]=[C:11]([C:14]3[CH:29]=[C:28]([CH3:30])[C:17]([O:18][CH2:19][CH:20]([OH:27])[CH2:21][NH:22][C:23](=[O:26])[CH2:24][OH:25])=[C:16]([CH3:31])[CH:15]=3)[N:10]=2)C=CC=1)=O.[CH3:32][N:33]([CH2:35][C:36]1[CH:44]=[CH:43][C:39]([C:40]([OH:42])=O)=[CH:38][C:37]=1[O:45][CH3:46])[CH3:34].OCC(NCC(O)COC1C(C)=CC(C(=N)NO)=CC=1C)=O.C([O-])=O>>[CH3:34][N:33]([CH2:35][C:36]1[CH:44]=[CH:43][C:39]([C:40]2[O:42][N:12]=[C:11]([C:14]3[CH:15]=[C:16]([CH3:31])[C:17]([O:18][CH2:19][CH:20]([OH:27])[CH2:21][NH:22][C:23](=[O:26])[CH2:24][OH:25])=[C:28]([CH3:30])[CH:29]=3)[N:10]=2)=[CH:38][C:37]=1[O:45][CH3:46])[CH3:32]

Participants

5

Reactant 4

HCID 283FormateHCID 211828904-Dimethylaminomethyl-3-methoxy-benzoic acidHCID 87208794HCID 87208794, compoundHCID 178426660HCID 178426660, compound

Product 1

HCID 66932285rac-N-(3-{4-[5-(4-dimethylaminomethyl-3-methoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

Procedure

The title compound was prepared in analogy to rac-N-(3-{4-[5-(3-formyl-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide, starting from 4-dimethylaminomethyl-3-methoxy-benzoic acid and rac-2-hydroxy-N-{2-hydroxy-3-[4-(N-hydroxycarbamimidoyl)-2,6-dimethyl-phenoxy]-propyl}-acetamide. LC-MS: tR=0.71 min; [M+1]+=485.27; 1H NMR (CDCl3): δ2.36 (s, 6H), 2.54 (s, 6H), 3.45-3.54 (m, 1H), 3.74-3.91 (m, 3H), 3.92 (s, 2H), 4.01 (s, 3H), 4.15-4.20 (m, 3H), 7.13 (t, J=5.8 Hz, 1H), 7.60 (d, J=8.0 Hz, 1H), 7.72 (s, 1H), 7.81-7.86 (m, 3H), 8.50 (s, 1H) (as formate salt).

Sources & evidence

ORD record
ord-91bb74cdd1d949e695ba01ea8cf30481
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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