Methanol → 5-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid ((-)-2,2,2-trifluoro-1-pyridin-2-yl-ethyl)-amide

HRID 632296Notes

Reaction equation

HRID 632296 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.[F:18][C:19]([F:29])([F:28])[CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[NH2:21].CO>CCCCCCC>[F:29][C:19]([F:18])([F:28])[CH:20]([NH:21][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])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 252199112,2,2-Trifluoro-1-(pyridin-2-yl)ethan-1-amineHCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 780101485-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid ((-)-2,2,2-trifluoro-1-pyridin-2-yl-ethyl)-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 α-(trifluoromethyl)-2-pyridinemethanamine (CAN 503173-14-6) as starting materials. The product was isolated by chiral chromatography on Reprosil Chiral NR using heptane/20% ethanol as eluent. The (S)-(−)-enantiomer was isolated. LC-MS (UV peak area/ESI) 100%, 392.1950 (M+H)+; αD20 (MeOH)=−91.1°.

Workup

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

Sources & evidence

ORD record
ord-3b71bac50083494193fd33bdb0732a85
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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