N-((S)-3-{2-ethyl-4-[5-(2-ethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide → Rac-n-(3-{2,6-dimethyl-4-[5-(6-methyl-2-methylamino-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 2069432Notes

Reaction equation

HRID 2069432 reaction equation
[CH2:1]([C:3]1[CH:18]=[C:17]([C:19]2[N:23]=[C:22]([C:24]3[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([NH:31][CH2:32]C)[N:25]=3)[O:21][N:20]=2)[CH:16]=[C:15]([CH3:34])[C:4]=1[O:5][CH2:6][C@@H:7]([OH:14])[CH2:8][NH:9][C:10](=[O:13])[CH2:11][OH:12])C.CC1N=C(NC)N=C(C(O)=O)C=1.OCC(NCC(O)COC1C(C)=CC(C(=N)NO)=CC=1C)=O>>[CH3:34][C:15]1[CH:16]=[C:17]([C:19]2[N:23]=[C:22]([C:24]3[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([NH:31][CH3:32])[N:25]=3)[O:21][N:20]=2)[CH:18]=[C:3]([CH3:1])[C:4]=1[O:5][CH2:6][CH:7]([OH:14])[CH2:8][NH:9][C:10](=[O:13])[CH2:11][OH:12]

Participants

4

Reactant 3

HCID 42606908N-((S)-3-{2-ethyl-4-[5-(2-ethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamideHCID 669338436-Methyl-2-(methylamino)pyrimidine-4-carboxylic acidHCID 178426660HCID 178426660, compound

Product 1

HCID 42606906Rac-n-(3-{2,6-dimethyl-4-[5-(6-methyl-2-methylamino-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

Procedure

rac-N-(3-{2,6-Dimethyl-4-[5-(6-methyl-2-methylamino-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide is prepared in analogy to N—((S)-3-{2-ethyl-4-[5-(2-ethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide using 6-methyl-2-methylamino-pyrimidine-4-carboxylic acid and 2-hydroxy-N-{2-hydroxy-3-[4-(N-hydroxycarbamimidoyl)-2,6-dimethyl-phenoxy]-propyl}-acetamide; LC-MS: tR=0.85 min; [M+H]+=443.21.

Sources & evidence

ORD record
ord-11dd1eed4bb44146b219eb367e4198fb
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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