Methanol → HCID 78010153, compound

HRID 927689Notes

Reaction equation

HRID 927689 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.[NH2:18][CH:19]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:20]#[N:21].CO>CCCCCCC>[C:20]([CH:19]([NH:18][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])[CH2:22][CH:23]([CH3:25])[CH3:24])#[N:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 13352438HCID 13352438, compoundHCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 78010153HCID 78010153, 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 2-amino-4-methyl-pentanenitrile (CAN 65451-12-9) 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%, 328.2026 (M+H)+, αD20 (MeOH)=−8.0°.

Workup

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

Sources & evidence

ORD record
ord-c43f5cab12614784813605ee053b6c89
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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