N1-(4-{[2-methyl-5-(methyloxy)phenyl]oxy}phenyl)-D-alaninamide → (5R)-5-methyl-3-(6-{[2-methyl-5-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione

HRID 1023605Notes

Reaction equation

HRID 1023605 reaction equation
CC1C=C[C:5]([O:8]C)=CC=1OC1C=CC(NC(=O)[C@@H](C)N)=CC=1.[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=1[O:32][C:33]1[N:38]=[CH:37][C:36]([NH:39][C:40](=[O:44])[C@@H:41]([CH3:43])[NH2:42])=[CH:35][CH:34]=1>>[CH3:43][C@H:41]1[NH:42][C:5](=[O:8])[N:39]([C:36]2[CH:37]=[N:38][C:33]([O:32][C:25]3[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:24]=3[CH3:23])=[CH:34][CH:35]=2)[C:40]1=[O:44]

Participants

3

Reactant 2

HCID 67235021N1-(4-{[2-methyl-5-(methyloxy)phenyl]oxy}phenyl)-D-alaninamideHCID 67235532HCID 67235532, compound2×

Product 1

HCID 53241720(5R)-5-methyl-3-(6-{[2-methyl-5-(methyloxy)phenyl]oxy}-3-pyridinyl)-2,4-imidazolidinedione

Procedure

The title compound was made in a similar fashion to the preparation of Example 7 replacing N1-(4-{[2-methyl-5-(methyloxy)phenyl]oxy}phenyl)-D-alaninamide with N1-(6-{[2-methyl-5-(methyloxy)phenyl]oxy}-3-pyridinyl)-D-alaninamide (Intermediate 56, 118 mg) to afford the title compound (78 mg)

Sources & evidence

ORD record
ord-338e288d2af941c1a84a503a4687f364
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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