HCID 90202747, compound → HCID 123768986, compound

HRID 1480122Notes

Reaction equation

HRID 1480122 reaction equation
[CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.Cl.[NH2:20][CH:21]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:22][C:23]([NH2:25])=[O:24]>>[C:23]([CH2:22][CH:21]([NH:20][C:10]([C:7]1[CH:6]=[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:4]([CH:1]2[CH2:2][CH2:3]2)=[CH:9][N:8]=1)=[O:12])[CH2:26][CH:27]([CH3:29])[CH3:28])(=[O:24])[NH2:25]

Participants

3

Reactant 2

HCID 90202747HCID 90202747, compoundHCID 902036745-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

Product 1

HCID 123768986HCID 123768986, compound

Procedure

The title compound was synthesized in analogy to Example 63b, using 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (Example 48c) and 3-amino-5-methylhexanamide hydrochloride (CAN 93169-29-0) as starting materials to yield the racemate mixture. The racemate was separated into its enantiomers by preparative chiral HPLC (Chiralpak AD, isopropanol/heptane) and the title compound was the first enantiomer collected and isolated as colorless oil; MS (ESI, m/z): 388.0 (M+H+).

Workup

  1. customto yield the racemate mixture
  2. customThe racemate was separated into its enantiomers by preparative chiral HPLC (Chiralpak AD, isopropanol/heptane)
  3. customcollected
  4. customisolated as colorless oil

Sources & evidence

ORD record
ord-66a8232b6e474773b57fd8166567a393
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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