Methanol → 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid ((-)-cyano-methyl-methyl)-amide

HRID 632302Notes

Reaction equation

HRID 632302 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.[NH2:19][CH:20]([CH3:23])[C:21]#[N:22].CO>CCCCCCC>[C:21]([CH:20]([NH:19][C:15]([C:7]1[CH:6]=[CH:5][C:4]([CH:1]2[CH2:2][CH2:3]2)=[C:9]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14]2)[N:8]=1)=[O:17])[CH3:23])#[N:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 127828772-Aminopropanenitrile hydrochlorideHCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 780101525-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid ((-)-cyano-methyl-methyl)-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 2-amino-propanenitrile monohydrochloride (CAN 2134-48-7) as starting materials. The product was isolated by chiral chromatography on Reprosil Chiral NR using heptane/15% ethanol as eluent. The (−)-enantiomer was isolated. LC-MS (UV peak area/ESI) 100%, 286.1552 (M+H)+, αD20 (MeOH)=−9.6°.

Workup

  1. customThe product was isolated by chiral chromatography on Reprosil Chiral NR
  2. customThe (−)-enantiomer was isolated

Sources & evidence

ORD record
ord-9c332ce8bb3b44a1960cfa345f0db28f
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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