Methanol → HCID 78010200, compound

HRID 927843Notes

Reaction equation

HRID 927843 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][C:7]=2[N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)[CH2:3][CH2:2]1.[NH2:21][CH:22]([CH:26]1[CH2:28][CH2:27]1)[C:23]([NH2:25])=[O:24].CO>CCCCCCC>[C:23]([CH:22]([NH:21][C:12]([C:10]1[CH:9]=[CH:8][C:7]([N:15]2[CH2:18][C:17]([F:20])([F:19])[CH2:16]2)=[C:6]([O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[N:11]=1)=[O:14])[CH:26]1[CH2:28][CH2:27]1)(=[O:24])[NH2:25]

Participants

5

Reactant 3

HCID 887MethanolHCID 61310151HCID 61310151, compoundHCID 710872926-(Cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)picolinic acid

Product 1

HCID 78010200HCID 78010200, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

The title compound was synthesized in analogy to Example 1, using 6-cyclopropylmethyloxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid (Example 69b) and α-amino-cyclopropaneacetamide (CAN 1100749-41-4) as starting materials. The product was isolated by chiral chromatography on Chiralpak AD using heptane/40% ethanol as eluent. The (+)-enantiomer was isolated. LC-MS (UV peak area/ESI) 100%, 381.1739 (M+H)+, αD20 (MeOH)=+35.0°.

Workup

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

Sources & evidence

ORD record
ord-c6e1688109094cf2823f03d126495f86
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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