Methanol → HCID 78010150, compound

HRID 927686Notes

Reaction equation

HRID 927686 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.Cl.[CH2:19]([CH:21]([C:23]1[N:27]=[C:26]([CH3:28])[O:25][N:24]=1)[NH2:22])[CH3:20].CO>CCCCCCC>[CH3:28][C:26]1[O:25][N:24]=[C:23]([CH:21]([NH:22][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])[CH2:19][CH3:20])[N:27]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14024497111997-68-3HCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 78010150HCID 78010150, compound

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-ethyl-5-methyl-1,2,4-oxadiazole-3-methanamine hydrochloride (1:1) (CAN 111997-68-3) as starting materials. The product was isolated by chiral chromatography on Chiralpak AD using heptane/8% ethanol as eluent. The (+)-enantiomer was isolated. LC-MS (UV peak area/ESI) 98.5%, 357.1925 (M+H)+, αD20 (MeOH)=+36.7°.

Workup

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

Sources & evidence

ORD record
ord-207b1320eff64154a3fe3fc582abf75e
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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