Methanol → 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid [(-)-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

HRID 927683Notes

Reaction equation

HRID 927683 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:15]([OH:17])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH2:3][CH2:2]1.[CH3:18][CH:19]([C:21]1[N:25]=[C:24]([CH3:26])[O:23][N:22]=1)[NH2:20].CO>CCCCCCC>[CH3:26][C:24]1[O:23][N:22]=[C:21]([CH:19]([NH:20][C:15]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]3[CH2:2][CH2:3]3)=[C:9]([O:10][CH2:11][CH:12]3[CH2:13][CH2:14]3)[N:8]=2)=[O:17])[CH3:18])[N:25]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 435592951-(5-Methyl-1,2,4-oxadiazol-3-yl)ethan-1-amineHCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 780101495-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid [(-)-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

The title compound was synthesized in analogy to Example 1, using 5-cyclopropyl-6-cyclopropylmethyloxy-pyridine-2-carboxylic acid (Example 42a) and α,5-dimethyl-1,2,4-oxadiazole-3-methanamine (CAN 1153834-40-2) as starting materials. The product was isolated by chiral chromatography on Chiralpak AD using heptane/20% ethanol as eluent. The (−)-enantiomer was isolated. LC-MS (UV peak area/ESI) 98.1%, 343.1767 (M+H)+, αD20 (MeOH)=−28.2°.

Workup

  1. customThe product was isolated by chiral chromatography on Chiralpak AD
  2. customThe (−)-enantiomer was isolated

Sources & evidence

ORD record
ord-6fa039b92dd84b0d995efe76415b8cb7
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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