2-Cyclopentyl-6-methoxyisonicotinic acid → (S)-3-{2-Chloro-4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-propane-1,2-diol

HRID 245110Notes

Reaction equation

HRID 245110 reaction equation
[CH:1]1([C:6]2[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH3:16])[N:14]=2)[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:25]=[C:26]([CH3:37])[C:27]=1[O:28][CH2:29][C@@H:30]1[CH2:34][O:33]C(C)(C)[O:31]1)[C:21]([NH:23]O)=[NH:22]>>[Cl:17][C:18]1[CH:19]=[C:20]([C:21]2[N:23]=[C:9]([C:8]3[CH:12]=[C:13]([O:15][CH3:16])[N:14]=[C:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:7]=3)[O:11][N:22]=2)[CH:25]=[C:26]([CH3:37])[C:27]=1[O:28][CH2:29][C@@H:30]([OH:31])[CH2:34][OH:33]

Participants

3

Reactant 2

HCID 584180372-Cyclopentyl-6-methoxyisonicotinic acidHCID 178426667(R)-3-Chloro-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-N-hydroxy-5-methyl-benzamidine

Product 1

HCID 49872160(S)-3-{2-Chloro-4-[5-(2-cyclopentyl-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 1 starting from 2-cyclopentyl-6-methoxy-isonicotinic acid and (R)-3-chloro-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-N-hydroxy-5-methyl-benzamidine; LC-MS**: tR=0.89 min, [M+H]+=460.18; 1H NMR (CDCl3): δ 1.72-1.80 (m, 2H), 1.84-1.95 (m, 4H), 2.03 (t br, J=5.8 Hz, 1H), 2.07-2.16 (m, 2H), 2.45 (s, 3H), 2.80 (d br, J=5.0 Hz, 1H), 3.20-3.29 (m, 1H), 3.83-3.93 (m, 2H), 4.02 (s, 3H), 4.11-4.14 (m, 2H), 4.15-4.21 (m, 1H), 7.30 (d, J=1.0 Hz, 1H), 7.50 (d, J=0.8 Hz, 1H), 7.95 (d, J=1.8 Hz, 1H), 8.09 (d, J=1.8 Hz, 1H).

Sources & evidence

ORD record
ord-8858e04632244a03a1fdce6472b5e23d
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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