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

HRID 632280Notes

Reaction equation

HRID 632280 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][C@H:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:21]([NH:23][CH3:24])=[O:22].CO>CCCCCCC>[CH3:24][NH:23][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])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 71087301(2R)-2-amino-N-methyl-2-phenylacetamide hydrochlorideHCID 710873465-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 780121885-Cyclopropyl-6-cyclopropylmethoxy-pyridine-2-carboxylic acid ((-)-methylcarbamoyl-phenyl-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 42 a) and (αR)-α-amino-N-methyl-benzeneacetamide hydrochloride (1:1) (CAN 97549-10-5) as starting materials. Racemization occurred during the synthesis and the product was isolated by chiral chromatography on Chiralpak AD using heptane/20% ethanol as eluent. The (−)-enantiomer was isolated. LC-MS (UV peak area/ESI) 100%, 380.1968 (M+H)+, αD20 (MeOH)=−6.0°.

Workup

  1. customRacemization occurred during the synthesis
  2. customthe product was isolated by chiral chromatography on Chiralpak AD
  3. customThe (−)-enantiomer was isolated

Sources & evidence

ORD record
ord-25ce21494def4c18b2cf5d3ae444db82
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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