alpha-Chlorohydrin, (+)- → (S)-3-{2-Chloro-4-[5-(2-cyclohexyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propane-1,2-diol

HRID 245125Notes

Reaction equation

HRID 245125 reaction equation
[CH:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[C:14]([O:16][CH3:17])[N:15]=2)[C:10]([OH:12])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:26]=[C:27]([CH3:30])[C:28]=1[OH:29])[C:22]([NH:24]O)=[NH:23].Cl[CH2:32][C@@H:33]([OH:36])[CH2:34][OH:35]>>[Cl:18][C:19]1[CH:20]=[C:21]([C:22]2[N:24]=[C:10]([C:9]3[CH:13]=[C:14]([O:16][CH3:17])[N:15]=[C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)[CH:8]=3)[O:12][N:23]=2)[CH:26]=[C:27]([CH3:30])[C:28]=1[O:29][CH2:32][C@@H:33]([OH:36])[CH2:34][OH:35]

Participants

4

Reactant 3

HCID 148904alpha-Chlorohydrin, (+)-HCID 67491148HCID 67491148, compoundHCID 178426665HCID 178426665, compound

Product 1

HCID 67491206(S)-3-{2-Chloro-4-[5-(2-cyclohexyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propane-1,2-diol

Procedure

The title compound is prepared in analogy to Example 3 starting from 2-cyclohexyl-6-methoxy-isonicotinic acid, 3-chloro-4,N-dihydroxy-5-methyl-benzamidine and (S)-3-chloro-1,2-propanediol; LC-MS**: tR=1.01 min, [M+H]+=473.95; 1H NMR (CDCl3): δ: 8.08 (s, 1H), 7.94 (s, 1H), 7.48 (s, 1H), 7.30 (s, 1H), 4.18 (m, 1H), 4.10-4.14 (m, 2H), 4.03 (s, 3H), 3.84-3.95 (m, 2H), 2.84 (s br, 1H), 2.69-2.80 (m, 1H), 2.45 (s, 3H), 1.99-2.13 (m, 2H), 1.86-1.96 (m, 2H), 1.76-1.84 (m, 1H), 1.15-1.68 (m, 6H).

Sources & evidence

ORD record
ord-17f4d59e53864a87973a746fab00d37a
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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